Regio- and stereoselective acylation of saturated carbocycles via Norrish–Yang photocyclization
A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish–Yang photocyclization of 1,2-diketones and subsequent ring opening of the α-hydroxy-cyclobutanones. The C–H activation of the carbocycle proceeds regioselectively at vic...
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| Published in | Tetrahedron letters Vol. 51; no. 5; pp. 872 - 874 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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03.02.2010
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| Abstract | A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish–Yang photocyclization of 1,2-diketones and subsequent ring opening of the α-hydroxy-cyclobutanones. The C–H activation of the carbocycle proceeds regioselectively at vicinal to the diketone moiety resulting in stereoselective formation of
cis-fused bicycles. The following C–C cleavage affords vicinally
cis-acylated carbocycles. Predictability, generality, and practicality of the present strategy have been demonstrated using variously modified saturated carbocycles. |
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| AbstractList | A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish-Yang photocyclization of 1,2-diketones and subsequent ring opening of the alpha-hydroxy-cyclobutanones. The C-H activation of the carbocycle proceeds regioselectively at vicinal to the diketone moiety resulting in stereoselective formation of cis-fused bicycles. The following C-C cleavage affords vicinally cis-acylated carbocycles. Predictability, generality, and practicality of the present strategy have been demonstrated using variously modified saturated carbocycles. (C) 2009 Elsevier Ltd. All rights reserved. A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish–Yang photocyclization of 1,2-diketones and subsequent ring opening of the α-hydroxy-cyclobutanones. The C–H activation of the carbocycle proceeds regioselectively at vicinal to the diketone moiety resulting in stereoselective formation of cis-fused bicycles. The following C–C cleavage affords vicinally cis-acylated carbocycles. Predictability, generality, and practicality of the present strategy have been demonstrated using variously modified saturated carbocycles. |
| Author | Inoue, Masayuki Kamijo, Shin Hoshikawa, Tamaki |
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| Cites_doi | 10.1021/cr030616h 10.1055/s-2007-984523 10.1021/ar9000058 10.1016/j.tet.2005.11.027 10.1080/00397910500334629 10.1021/ja011540e 10.1038/nature06485 10.1021/ar800164n 10.1021/jo702663w 10.1002/anie.200806273 10.1021/cr0680336 10.1002/hlca.200690228 10.1248/cpb.27.1679 10.1016/S0040-4039(00)84477-9 10.1021/jo00253a033 10.1002/1615-4169(200107)343:5<393::AID-ADSC393>3.0.CO;2-K 10.1021/ja01544a092 10.1021/jo00332a045 10.1021/ja01048a045 10.1016/S0040-4039(00)86864-1 10.1002/hlca.19880710125 10.1248/cpb.25.3354 10.1007/BF02498161 10.1021/ja00860a034 10.1039/a902384d |
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| Keywords | FUNCTIONALIZATION STEREOCONTROLLED PHOTOCYCLIZATION KETONES 1,2-DIKETONES ADAMANTANES PHOTOCHEMICAL-REACTIONS ALKANES |
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| References | bib9 Zhang, Li (bib11) 2006; 36 bib8 Wagner, Wessig, Mühling (bib4) 2005 Urry, Trecker, Turro, Lee, Hirao, Unno, Miura, Yonemitsu, Obayashi, Mizuta, Noguchi, Hamer, Sarphatie, Verheijdt, Cerfontain, Hamer, Herrera, Rondón, Suárez, Herrera, Rondón, Suárez (bib6) 1962; 84 Fukunishi, Kohno, Kojo, Kishi, Kato, Sakaguchi, Ishii, Akhrem, Churilova, Orlinkov, Afanas’eva, Vitt, Petrovskii, Chatani, Asaumi, Yorimitsu, Ikeda, Kakiuchi, Murai, Uenoyama, Fukuyama, Morimoto, Nobuta, Nagai, Ryu (bib2) 1988; 53 Hoffmann (bib5) 2008; 108 Carlsen, Katsuki, Martin, Sharpless, Zibuck, Seebach (bib7) 1981; 46 Yang, Yang (bib3) 1958; 80 bib10 Ishii, Sakaguchi, Iwahama, Knorr, Dick, Sanford, Davies, Manning, Chen, Engle, Wang, Yu, Li, Daugulis, Do, Shabashov (bib1) 2005; vols. 1-2 Ishii, Y (WOS:000170369800004) 2001; 343 ZIBUCK, R (WOS:A1988M061300024) 1988; 71 DYKER G (WOS:000274430100027.8) 2005; 1 Daugulis, O (WOS:000269308800009) 2009; 42 Uenoyama, Y (WOS:000241928300032) 2006; 89 HIRAO, KI (WOS:A1977EH39200031) 1977; 25 Zhang, XX (WOS:000234544600016) 2006; 36 OBAYASHI, M (WOS:A1979HF86200025) 1979; 27 Akhrem, IS (WOS:000074866300022) 1998; 47 SARPHATIE, LA (WOS:A1983PZ40400002) 1983; 102 URRY, WH (WOS:A19623072B00031) 1962; 84 FUKUNISHI, K (WOS:A1988P985100033) 1988; 53 Chen, X (WOS:000267809800005) 2009; 48 TURRO, NJ (WOS:A1969E187900045) 1969; 91 HAMER, NK (WOS:A1982MZ21700032) 1982; 23 Davies, HML (WOS:000252554100035) 2008; 451 Li, CJ (WOS:000263428300012) 2009; 42 Herrera, AJ (WOS:000249168300005) 2007 Chatani, N (WOS:000172049200019) 2001; 123 Wagner, PJ (CCC:000228482200002) 2005; 12 YANG, NC (WOS:A1958WB38600092) 1958; 80 HAMER, NK (WOS:A1986C261500027) 1986; 27 CARLSEN, PHJ (WOS:A1981MF16700045) 1981; 46 Dick, AR (WOS:000235763900001) 2006; 62 Wessig, P (CCC:000228482200003) 2005; 12 Kishi, A (WOS:000081763800033) 1999 Herrera, AJ (WOS:000255339600009) 2008; 73 Hoffmann, N (WOS:000253947800004) 2008; 108 Knorr, R (WOS:000223812900004) 2004; 104 Chen (10.1016/j.tetlet.2009.12.027_bib1f) 2009; 48 Uenoyama (10.1016/j.tetlet.2009.12.027_bib2e) 2006; 89 Hoffmann (10.1016/j.tetlet.2009.12.027_bib5) 2008; 108 Li (10.1016/j.tetlet.2009.12.027_bib1g) 2009; 42 Hamer (10.1016/j.tetlet.2009.12.027_bib6g) 1986; 27 Hirao (10.1016/j.tetlet.2009.12.027_bib6c) 1977; 25 Herrera (10.1016/j.tetlet.2009.12.027_bib6i) 2008; 73 (10.1016/j.tetlet.2009.12.027_bib1a) 2005; vols. 1-2 Ishii (10.1016/j.tetlet.2009.12.027_bib1b) 2001; 343 Knorr (10.1016/j.tetlet.2009.12.027_bib1c) 2004; 104 Carlsen (10.1016/j.tetlet.2009.12.027_bib7a) 1981; 46 Dick (10.1016/j.tetlet.2009.12.027_bib1d) 2006; 62 Fukunishi (10.1016/j.tetlet.2009.12.027_bib2a) 1988; 53 Turro (10.1016/j.tetlet.2009.12.027_bib6b) 1969; 91 Hamer (10.1016/j.tetlet.2009.12.027_bib6e) 1982; 23 Davies (10.1016/j.tetlet.2009.12.027_bib1e) 2008; 451 Herrera (10.1016/j.tetlet.2009.12.027_bib6h) 2007 Sarphatie (10.1016/j.tetlet.2009.12.027_bib6f) 1983; 102 Wessig (10.1016/j.tetlet.2009.12.027_bib4b) 2005 Daugulis (10.1016/j.tetlet.2009.12.027_bib1h) 2009; 42 Akhrem (10.1016/j.tetlet.2009.12.027_bib2c) 1998; 47 Wagner (10.1016/j.tetlet.2009.12.027_bib4a) 2005 Zibuck (10.1016/j.tetlet.2009.12.027_bib7b) 1988; 71 Urry (10.1016/j.tetlet.2009.12.027_bib6a) 1962; 84 Yang (10.1016/j.tetlet.2009.12.027_bib3) 1958; 80 Obayashi (10.1016/j.tetlet.2009.12.027_bib6d) 1979; 27 Zhang (10.1016/j.tetlet.2009.12.027_bib11) 2006; 36 Kishi (10.1016/j.tetlet.2009.12.027_bib2b) 1999 Chatani (10.1016/j.tetlet.2009.12.027_bib2d) 2001; 123 |
| References_xml | – volume: 80 start-page: 2913 year: 1958 ident: bib3 publication-title: J. Am. Chem. Soc. contributor: fullname: Yang – volume: 53 start-page: 4369 year: 1988 ident: bib2 publication-title: J. Org. Chem. contributor: fullname: Ryu – volume: 108 start-page: 1052 year: 2008 ident: bib5 publication-title: Chem. Rev. contributor: fullname: Hoffmann – volume: 84 start-page: 118 year: 1962 ident: bib6 publication-title: J. Am. Chem. Soc. contributor: fullname: Suárez – volume: vols. 1-2 start-page: 393 year: 2005 ident: bib1 publication-title: Handbook of C–H Transformations contributor: fullname: Shabashov – ident: bib8 – ident: bib9 – start-page: 11 year: 2005 end-page: 39 ident: bib4 publication-title: Synthetic Organic Photochemistry contributor: fullname: Mühling – volume: 46 start-page: 3936 year: 1981 ident: bib7 publication-title: J. Org. Chem. contributor: fullname: Seebach – ident: bib10 – volume: 36 start-page: 249 year: 2006 ident: bib11 publication-title: Synth. Commun. contributor: fullname: Li – volume: 104 start-page: 3795 year: 2004 ident: WOS:000223812900004 article-title: Alkylidenecarbenes, alkylidenecarbenoids, and competing species: Which is responsible for vinylic nucleophilic substitution, [1+2] cycloadditions, 1,5-CH insertions, and the Fritsch-Buttenberg-Wiechell rearrangement? publication-title: CHEMICAL REVIEWS doi: 10.1021/cr030616h contributor: fullname: Knorr, R – start-page: 1851 year: 2007 ident: WOS:000249168300005 article-title: Stereocontrolled photocyclization of 1,2-diketones applied to carbohydrate models: A new entry to C-ketosides publication-title: SYNLETT doi: 10.1055/s-2007-984523 contributor: fullname: Herrera, AJ – volume: 42 start-page: 1074 year: 2009 ident: WOS:000269308800009 article-title: Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar9000058 contributor: fullname: Daugulis, O – volume: 27 start-page: 1679 year: 1979 ident: WOS:A1979HF86200025 article-title: PHOTO-CHEMICAL REACTION OF 21-METHYL-20,21-DIKETOSTEROIDS - FORMATION OF NEW 3',4',16-ALPHA,17-ALPHA-TETRAHYDROCYCLOBUT[16,17]ANDROSTANES publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: OBAYASHI, M – volume: 12 start-page: 41 year: 2005 ident: CCC:000228482200003 article-title: Abstraction of (gamma +/- n)-hydrogen by excited carbonyls publication-title: SYNTHETIC ORGANIC PHOTOCHEMISTRY contributor: fullname: Wessig, P – volume: 80 start-page: 2913 year: 1958 ident: WOS:A1958WB38600092 article-title: PHOTOCHEMICAL REACTIONS OF KETONES IN SOLUTION publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: YANG, NC – volume: 62 start-page: 2439 year: 2006 ident: WOS:000235763900001 article-title: Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds publication-title: TETRAHEDRON doi: 10.1016/j.tet.2005.11.027 contributor: fullname: Dick, AR – volume: 71 start-page: 237 year: 1988 ident: WOS:A1988M061300024 article-title: NOTE ON THE PREPARATION OF 1,2-DIKETONES FROM ACETYLENES publication-title: HELVETICA CHIMICA ACTA contributor: fullname: ZIBUCK, R – volume: 12 start-page: 11 year: 2005 ident: CCC:000228482200002 article-title: Abstraction of gamma-hydrogens by excited carbonyls publication-title: SYNTHETIC ORGANIC PHOTOCHEMISTRY contributor: fullname: Wagner, PJ – volume: 46 start-page: 3936 year: 1981 ident: WOS:A1981MF16700045 article-title: A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: CARLSEN, PHJ – volume: 89 start-page: 2483 year: 2006 ident: WOS:000241928300032 article-title: Trifluoromethyl-radical-mediated carbonylation of alkanes leading to ethynyl ketones publication-title: HELVETICA CHIMICA ACTA contributor: fullname: Uenoyama, Y – volume: 102 start-page: 9 year: 1983 ident: WOS:A1983PZ40400002 article-title: PHOTOCHEMISTRY OF 1,2-DIKETONES .3. ON THE LUMINESCENCE AND PHOTOCHEMISTRY OF THE LOWER EXCITED ELECTRONIC STATES OF SOME ACYCLIC 1,2-DIKETONES publication-title: RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY contributor: fullname: SARPHATIE, LA – volume: 47 start-page: 918 year: 1998 ident: WOS:000074866300022 article-title: A new efficient and selective synthesis of ketones from alkanes or cycloalkanes, CO, and silanes in the presence of aprotic superacids publication-title: RUSSIAN CHEMICAL BULLETIN contributor: fullname: Akhrem, IS – volume: 343 start-page: 393 year: 2001 ident: WOS:000170369800004 article-title: Innovation of hydrocarbon oxidation with molecular oxygen and related reactions publication-title: ADVANCED SYNTHESIS & CATALYSIS contributor: fullname: Ishii, Y – volume: 36 start-page: 249 year: 2006 ident: WOS:000234544600016 article-title: Acid-promoted ring opening of alpha-hydroxyl cyclobutanones: A novel and facile one-pot synthesis of nitrile derivatives publication-title: SYNTHETIC COMMUNICATIONS doi: 10.1080/00397910500334629 contributor: fullname: Zhang, XX – volume: 84 start-page: 118 year: 1962 ident: WOS:A19623072B00031 article-title: PHOTOCHEMICAL REACTIONS OF 1,2-DIKETONES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: URRY, WH – volume: 123 start-page: 10935 year: 2001 ident: WOS:000172049200019 article-title: Ru-3(CO)(12)-catalyzed coupling reaction of sp(3) C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja011540e contributor: fullname: Chatani, N – volume: 451 start-page: 417 year: 2008 ident: WOS:000252554100035 article-title: Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion publication-title: NATURE doi: 10.1038/nature06485 contributor: fullname: Davies, HML – volume: 25 start-page: 3354 year: 1977 ident: WOS:A1977EH39200031 article-title: SINGLET AND TRIPLET EXCITED-STATE PHOTOCHEMISTRY OF TRICYCLO-[5.2.2.02,6]UNDECA-3,10-DIEN-9-ONE DERIVATIVES publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: HIRAO, KI – volume: 23 start-page: 473 year: 1982 ident: WOS:A1982MZ21700032 article-title: PHOTOCYCLIZATION OF ALPHA-BROMOMETHYL-1,2-DIKETONES publication-title: TETRAHEDRON LETTERS contributor: fullname: HAMER, NK – volume: 42 start-page: 335 year: 2009 ident: WOS:000263428300012 article-title: Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar800164n contributor: fullname: Li, CJ – volume: 73 start-page: 3384 year: 2008 ident: WOS:000255339600009 article-title: Stereocontrolled photocyclization of 1,2-diketones: Application of a 1,3-acetyl group transfer methodology to carbohydrates publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo702663w contributor: fullname: Herrera, AJ – volume: 53 start-page: 4369 year: 1988 ident: WOS:A1988P985100033 article-title: PHOTOACETYLATION OF 2-SUBSTITUTED ADAMANTANES - STEREOCHEMISTRY AND SUBSTITUENT EFFECTS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: FUKUNISHI, K – start-page: 1421 year: 1999 ident: WOS:000081763800033 article-title: Catalytic radical acetylation of adamantanes with biacetyl by a cobalt salt under atmospheric dioxygen publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: Kishi, A – volume: 48 start-page: 5094 year: 2009 ident: WOS:000267809800005 article-title: Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200806273 contributor: fullname: Chen, X – volume: 1 year: 2005 ident: WOS:000274430100027.8 publication-title: HDB C H TRANSFORMATI contributor: fullname: DYKER G – volume: 27 start-page: 2167 year: 1986 ident: WOS:A1986C261500027 article-title: A NEW ROUTE TO CYCLOPENTANE-1,3-DIONES publication-title: TETRAHEDRON LETTERS contributor: fullname: HAMER, NK – volume: 108 start-page: 1052 year: 2008 ident: WOS:000253947800004 article-title: Photochemical reactions as key steps in organic synthesis publication-title: CHEMICAL REVIEWS doi: 10.1021/cr0680336 contributor: fullname: Hoffmann, N – volume: 91 start-page: 5651 year: 1969 ident: WOS:A1969E187900045 article-title: INTRAMOLECULAR PHOTOREDUCTION OF ALKYL ALPHA-DIKETONES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: TURRO, NJ – volume: 89 start-page: 2483 year: 2006 ident: 10.1016/j.tetlet.2009.12.027_bib2e publication-title: Helv. Chim. Acta doi: 10.1002/hlca.200690228 contributor: fullname: Uenoyama – volume: 27 start-page: 1679 year: 1979 ident: 10.1016/j.tetlet.2009.12.027_bib6d publication-title: Chem. Pharm. Bull. doi: 10.1248/cpb.27.1679 contributor: fullname: Obayashi – volume: 42 start-page: 1074 year: 2009 ident: 10.1016/j.tetlet.2009.12.027_bib1h publication-title: Acc. Chem. Res. doi: 10.1021/ar9000058 contributor: fullname: Daugulis – volume: 27 start-page: 2167 year: 1986 ident: 10.1016/j.tetlet.2009.12.027_bib6g publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)84477-9 contributor: fullname: Hamer – volume: vols. 1-2 year: 2005 ident: 10.1016/j.tetlet.2009.12.027_bib1a – volume: 451 start-page: 417 year: 2008 ident: 10.1016/j.tetlet.2009.12.027_bib1e publication-title: Nature doi: 10.1038/nature06485 contributor: fullname: Davies – volume: 53 start-page: 4369 year: 1988 ident: 10.1016/j.tetlet.2009.12.027_bib2a publication-title: J. Org. Chem. doi: 10.1021/jo00253a033 contributor: fullname: Fukunishi – start-page: 11 year: 2005 ident: 10.1016/j.tetlet.2009.12.027_bib4a contributor: fullname: Wagner – volume: 343 start-page: 393 year: 2001 ident: 10.1016/j.tetlet.2009.12.027_bib1b publication-title: Adv. Synth. Catal. doi: 10.1002/1615-4169(200107)343:5<393::AID-ADSC393>3.0.CO;2-K contributor: fullname: Ishii – volume: 42 start-page: 335 year: 2009 ident: 10.1016/j.tetlet.2009.12.027_bib1g publication-title: Acc. Chem. Res. doi: 10.1021/ar800164n contributor: fullname: Li – volume: 80 start-page: 2913 year: 1958 ident: 10.1016/j.tetlet.2009.12.027_bib3 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01544a092 contributor: fullname: Yang – volume: 48 start-page: 5094 year: 2009 ident: 10.1016/j.tetlet.2009.12.027_bib1f publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200806273 contributor: fullname: Chen – volume: 102 start-page: 9 year: 1983 ident: 10.1016/j.tetlet.2009.12.027_bib6f publication-title: J. R. Neth. Chem. Soc. contributor: fullname: Sarphatie – volume: 46 start-page: 3936 year: 1981 ident: 10.1016/j.tetlet.2009.12.027_bib7a publication-title: J. Org. Chem. doi: 10.1021/jo00332a045 contributor: fullname: Carlsen – volume: 108 start-page: 1052 year: 2008 ident: 10.1016/j.tetlet.2009.12.027_bib5 publication-title: Chem. Rev. doi: 10.1021/cr0680336 contributor: fullname: Hoffmann – volume: 91 start-page: 5651 year: 1969 ident: 10.1016/j.tetlet.2009.12.027_bib6b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01048a045 contributor: fullname: Turro – volume: 62 start-page: 2439 year: 2006 ident: 10.1016/j.tetlet.2009.12.027_bib1d publication-title: Tetrahedron doi: 10.1016/j.tet.2005.11.027 contributor: fullname: Dick – volume: 36 start-page: 249 year: 2006 ident: 10.1016/j.tetlet.2009.12.027_bib11 publication-title: Synth. Commun. doi: 10.1080/00397910500334629 contributor: fullname: Zhang – volume: 123 start-page: 10935 year: 2001 ident: 10.1016/j.tetlet.2009.12.027_bib2d publication-title: J. Am. Chem. Soc. doi: 10.1021/ja011540e contributor: fullname: Chatani – volume: 23 start-page: 473 year: 1982 ident: 10.1016/j.tetlet.2009.12.027_bib6e publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)86864-1 contributor: fullname: Hamer – start-page: 41 year: 2005 ident: 10.1016/j.tetlet.2009.12.027_bib4b contributor: fullname: Wessig – volume: 73 start-page: 3384 year: 2008 ident: 10.1016/j.tetlet.2009.12.027_bib6i publication-title: J. Org. Chem. doi: 10.1021/jo702663w contributor: fullname: Herrera – volume: 71 start-page: 237 year: 1988 ident: 10.1016/j.tetlet.2009.12.027_bib7b publication-title: Helv. Chim. Acta doi: 10.1002/hlca.19880710125 contributor: fullname: Zibuck – volume: 25 start-page: 3354 year: 1977 ident: 10.1016/j.tetlet.2009.12.027_bib6c publication-title: Chem. Pharm. Bull. doi: 10.1248/cpb.25.3354 contributor: fullname: Hirao – volume: 47 start-page: 918 year: 1998 ident: 10.1016/j.tetlet.2009.12.027_bib2c publication-title: Russ. Chem. Bull. doi: 10.1007/BF02498161 contributor: fullname: Akhrem – start-page: 1851 year: 2007 ident: 10.1016/j.tetlet.2009.12.027_bib6h publication-title: Synlett doi: 10.1055/s-2007-984523 contributor: fullname: Herrera – volume: 84 start-page: 118 year: 1962 ident: 10.1016/j.tetlet.2009.12.027_bib6a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00860a034 contributor: fullname: Urry – volume: 104 start-page: 3795 year: 2004 ident: 10.1016/j.tetlet.2009.12.027_bib1c publication-title: Chem. Rev. doi: 10.1021/cr030616h contributor: fullname: Knorr – start-page: 1421 year: 1999 ident: 10.1016/j.tetlet.2009.12.027_bib2b publication-title: Chem. Commun. doi: 10.1039/a902384d contributor: fullname: Kishi |
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| Snippet | A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish–Yang photocyclization of... A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish-Yang photocyclization of... |
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| Title | Regio- and stereoselective acylation of saturated carbocycles via Norrish–Yang photocyclization |
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