Asymmetric hydrosilylation of alkenes with alkoxyhydrosilanes catalyzed by chiral bis(oxazolinyl)phenyl-rhodium complex
Asymmetric addition of alkoxyhydrosilanes to styrene derivatives was examined with chiral bis(oxazolinyl)phenyl-rhodium complex to give moderate ratios (up to 77:23) of alpha- and beta-adducts and high enantioselectivity (up to 95% for the alpha-adduct).
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Published in | Synlett no. 12; pp. 2099 - 2102 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
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Abstract | Asymmetric addition of alkoxyhydrosilanes to styrene derivatives was examined with chiral bis(oxazolinyl)phenyl-rhodium complex to give moderate ratios (up to 77:23) of alpha- and beta-adducts and high enantioselectivity (up to 95% for the alpha-adduct). |
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AbstractList | Asymmetric addition of alkoxyhydrosilanes to styrene derivatives was examined with chiral bis(oxazolinyl)phenyl-rhodium complex to give moderate ratios (up to 77:23) of alpha- and beta-adducts and high enantioselectivity (up to 95% for the alpha-adduct). |
Author | Tsuchiya, Y Kobayashi, K Uchimura, H Nishiyama, H |
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Cites_doi | 10.1021/jo0257804 10.1021/ja017138h 10.1021/om020274q 10.1021/om0305162 10.1021/om011011j 10.1021/jo001614p 10.1021/ja025617q 10.1021/om010018y |
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Keywords | ORGANIC-SYNTHESIS AQUA COMPLEXES INTRAMOLECULAR HYDROSILATION STEREOCHEMISTRY asymmetric catalysis ALDOL-TYPE CONDENSATION ALCOHOLS CARBON BOND bisoxazoline hydrosilylation SILAFUNCTIONAL COMPOUNDS ENANTIOSELECTIVE ALLYLATION rhodium styrene |
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References | BERGENS, SH (WOS:A1992HJ25300028) 1992; 114 TAMAO, K (WOS:A1987K177800056) 1987; 52 Stark, MA (WOS:A1997XR61900041) 1997; 38 Jensen, JF (WOS:000175227600012) 2002; 124 UOZUMI, Y (WOS:A1995QQ90400003) 1995; 68 Hayashi, T (WOS:000167049700048) 2001; 66 Tamao, K (WOS:A1996VX65400033) 1996; 118 TAMAO, K (WOS:A1986E058400097) 1986; 108 Motoyama, Y (WOS:000078344000010) 1999 BERGENS, SH (WOS:A1992HJ25300029) 1992; 114 Motoyama, Y (WOS:000176724800018) 2002; 8 Motoyama, Y (WOS:000168395000013) 2001; 20 Denmark, SE (WOS:A1997WZ55500054) 1997; 62 UOZUMI, Y (WOS:A1991GW35600044) 1991; 113 Motoyama, Y (WOS:000177242200017) 2002; 21 Motoyama, Y (WOS:000175025900026) 2002; 21 Togni, A (WOS:000086016000019) 1999; 71 Motoyama, Y (WOS:000166687000007) 2001; 57 STARK MA (WOS:000224374600007.20) 2000; 57 Motoyama, Y (WOS:000082555300009) 1999; 18 HAYASHI, T (WOS:A1992KF18000012) 1992; 64 TAMAO, K (WOS:A1993LG15800046) 1993; 12 Pedersen, HL (WOS:000179110400007) 2002; 67 TAMAO, K (WOS:A1984TB97800017) 1984; 269 Fossey, JS (WOS:000188533800011) 2004; 23 WANG, XQ (WOS:A1994PR27900003) 1994; 13 Hayashi, T (WOS:000165350700002) 2000; 62 Tillack, A (WOS:000088285600016) 2000; 603 Motoyama, Y (WOS:A1997XX75300056) 1997 CURTIS, NR (WOS:A1992HC74200028) 1992; 33 TAMAO, K (WOS:A1983RR26300041) 1983; 2 Han, JW (WOS:000172939700026) 2001; 123 |
References_xml | – volume: 71 start-page: 1531 year: 1999 ident: WOS:000086016000019 article-title: Recent studies in asymmetric catalysis using ferrocenyl ligands publication-title: PURE AND APPLIED CHEMISTRY contributor: fullname: Togni, A – volume: 38 start-page: 5881 year: 1997 ident: WOS:A1997XR61900041 article-title: Synthesis and application of cationic 2,6-bis(2-oxazolinyl)phenylpalladium(II) complexes publication-title: TETRAHEDRON LETTERS contributor: fullname: Stark, MA – volume: 67 start-page: 7982 year: 2002 ident: WOS:000179110400007 article-title: Synthesis and application of arylmonophosphinoferrocene ligands: Ultrafast asymmetric hydrosilylation of styrene publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0257804 contributor: fullname: Pedersen, HL – volume: 57 start-page: 853 year: 2000 ident: WOS:000224374600007.20 publication-title: ORGANOMETALLICS contributor: fullname: STARK MA – volume: 18 start-page: 3584 year: 1999 ident: WOS:000082555300009 article-title: Stereochemistry in asymmetric alkylation of aldimine via chiral bis(oxazolyl)phenylplatinum complexes publication-title: ORGANOMETALLICS contributor: fullname: Motoyama, Y – volume: 123 start-page: 12915 year: 2001 ident: WOS:000172939700026 article-title: Palladium-catalyzed asymmetric hydrosilylation of 4-substituted 1-buten-3-ynes. 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STEREOCONTROL IN INTRAMOLECULAR HYDROSILATION OF ALLYL AND HOMOALLYL ALCOHOLS - A NEW APPROACH TO THE STEREOSELECTIVE SYNTHESIS OF 1,3-DIOL SKELETONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: TAMAO, K – volume: 114 start-page: 2128 year: 1992 ident: WOS:A1992HJ25300029 article-title: ASYMMETRIC CATALYSIS - MECHANISM OF ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROSILATION publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BERGENS, SH – volume: 23 start-page: 367 year: 2004 ident: WOS:000188533800011 article-title: Synthesis of 2,6-bis(2-oxazolinyl)phenylplatinum(II) NCN pincer complexes by direct cyclometalation. Catalysts for carbon-carbon bond formation publication-title: ORGANOMETALLICS doi: 10.1021/om0305162 contributor: fullname: Fossey, JS – volume: 21 start-page: 1684 year: 2002 ident: WOS:000175025900026 article-title: Formation of Fischer carbene complexes in asymmetric aldol-type condensation of an isocyanide component on bis(oxazolinyl)phenylrhodium(III) complexes with aldehydes: Stereochemistry, structural characterization, and mechanistic studies publication-title: ORGANOMETALLICS doi: 10.1021/om011011j contributor: fullname: Motoyama, Y – volume: 64 start-page: 1911 year: 1992 ident: WOS:A1992KF18000012 article-title: CATALYTIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ALCOHOLS VIA HYDROSILYLATION OF OLEFINS WITH A CHIRAL MONOPHOSPHINE-PALLADIUM CATALYST publication-title: PURE AND APPLIED CHEMISTRY contributor: fullname: HAYASHI, T – volume: 66 start-page: 1441 year: 2001 ident: WOS:000167049700048 article-title: Asymmetric hydrosilylation of styrenes catalyzed by palladium-MOP complexes: Ligand modification and mechanistic studies publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo001614p contributor: fullname: Hayashi, T – volume: 8 start-page: 2968 year: 2002 ident: WOS:000176724800018 article-title: Novel asymmetric Michael addition of alpha-cyanopropionates to acrolein by the use of a bis(oxazolinyl)phenylstannane-derived rhodium(III) complex as a chiral Lewis acid catalyst publication-title: CHEMISTRY-A EUROPEAN JOURNAL contributor: fullname: Motoyama, Y – volume: 269 start-page: C37 year: 1984 ident: WOS:A1984TB97800017 article-title: SILAFUNCTIONAL COMPOUNDS IN ORGANIC-SYNTHESIS .26. SILYL GROUPS SYNTHETICALLY EQUIVALENT TO THE HYDROXY GROUP publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: TAMAO, K – volume: 124 start-page: 4558 year: 2002 ident: WOS:000175227600012 article-title: Highly enantioselective hydrosilylation of aromatic alkenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja025617q contributor: fullname: Jensen, JF – volume: 62 start-page: 3 year: 2000 ident: WOS:000165350700002 article-title: Axially chiral monophosphine ligands (MOPs) and their use for palladium-catalyzed asymmetric hydrosilylation of olefins publication-title: CATALYSIS TODAY contributor: fullname: Hayashi, T – volume: 62 start-page: 3375 year: 1997 ident: WOS:A1997WZ55500054 article-title: Cyclopropanation with diazomethane and bis(oxazoline)palladium(II) complexes publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Denmark, SE – volume: 12 start-page: 2297 year: 1993 ident: WOS:A1993LG15800046 article-title: DEUTERIUM-LABELING STUDIES ON THE REGIOSELECTIVE AND STEREOSELECTIVE INTRAMOLECULAR HYDROSILATION OF ALLYL ALCOHOLS AND ALLYLAMINES CATALYZED BY PLATINUM AND RHODIUM COMPLEXES publication-title: ORGANOMETALLICS contributor: fullname: TAMAO, K – volume: 57 start-page: 853 year: 2001 ident: WOS:000166687000007 article-title: Asymmetric hetero Diels-Alder reaction of Danishefsky's dienes and glyoxylates with chiral bis(oxazolinyl)phenylrhodium(III) aqua complexes, and its mechanistic studies publication-title: TETRAHEDRON contributor: fullname: Motoyama, Y – volume: 20 start-page: 1580 year: 2001 ident: WOS:000168395000013 article-title: Bis(oxazolinyl)phenylrhodium(III) aqua complexes: Synthesis, structure, enantioselective allylation of aldehydes, and mechanistic studies publication-title: ORGANOMETALLICS doi: 10.1021/om010018y contributor: fullname: Motoyama, Y – volume: 114 start-page: 2121 year: 1992 ident: WOS:A1992HJ25300028 article-title: ASYMMETRIC CATALYSIS - PRODUCTION OF CHIRAL DIOLS BY ENANTIOSELECTIVE CATALYTIC INTRAMOLECULAR HYDROSILATION OF OLEFINS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BERGENS, SH – volume: 52 start-page: 4412 year: 1987 ident: WOS:A1987K177800056 article-title: SILAFUNCTIONAL COMPOUNDS IN ORGANIC-SYNTHESIS .35. 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Title | Asymmetric hydrosilylation of alkenes with alkoxyhydrosilanes catalyzed by chiral bis(oxazolinyl)phenyl-rhodium complex |
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