Copper Hydride- Catalyzed Tandem 1,4-Reduction/Alkylation Reactions
Exposure of an enone to a catalytic quantity of [CuH(PPh 3)] 6 in the presence of one of several silyl hydrides (PhMe 2SiH, PMHS, HMe 2SiOSiMe 2H) leads to conjugate reduction with concomitant formation of the corresponding silyl enol ether. Without isolation, treatment of these intermediates with a...
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| Published in | Tetrahedron Vol. 56; no. 18; pp. 2779 - 2788 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
28.04.2000
Elsevier |
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| Abstract | Exposure of an enone to a catalytic quantity of [CuH(PPh
3)]
6 in the presence of one of several silyl hydrides (PhMe
2SiH, PMHS, HMe
2SiOSiMe
2H) leads to conjugate reduction with concomitant formation of the corresponding silyl enol ether. Without isolation, treatment of these intermediates with a Lewis acid at low temperatures in the presence of an aldehyde, or with fluoride ion together with an activated halide, affords good yields of the product of 3-component coupling (3-CC) in a single reaction flask. |
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| AbstractList | Exposure of an enone to a catalytic quantity of [CuH(PPh
3)]
6 in the presence of one of several silyl hydrides (PhMe
2SiH, PMHS, HMe
2SiOSiMe
2H) leads to conjugate reduction with concomitant formation of the corresponding silyl enol ether. Without isolation, treatment of these intermediates with a Lewis acid at low temperatures in the presence of an aldehyde, or with fluoride ion together with an activated halide, affords good yields of the product of 3-component coupling (3-CC) in a single reaction flask. Exposure of an enone to a catalytic quantity of [CuH(PPh3)](6) in the presence of one of several silyl hydrides (PhMe2SiH, PMHS, HMe2SiOSiMe2H) leads to conjugate reduction with concomitant formation of the corresponding silyl enol ether. Without isolation, treatment of these intermediates with a Lewis acid at low temperatures in the presence of an aldehyde, or with fluoride ion together with an activated halide, affords good yields of the product of 3-component coupling (3-CC) in a single reaction flask. (C) 2000 Elsevier Science Ltd. All rights reserved. |
| Author | Papa, Patrick Sclafani, Joseph A. Keith, John M. Lipshutz, Bruce H. Chrisman, Will Noson, Kevin Vivian, Randall W. |
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| Cites_doi | 10.1021/ja00123a025 10.1016/S0040-4039(98)00855-7 10.1016/S0040-4020(99)00141-6 10.1021/jo00365a033 10.1021/ja00831a019 10.1021/jo00414a048 10.1016/S0040-4039(98)02130-3 |
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| Keywords | silyl hydrides copper hydride conjugate reduction KETONES NICKEL CHEMOSELECTIVE HYDROGENATION ALDOL REACTION <(PH3P)CUH>6 ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS ALPHA ALDEHYDES |
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| References | Pilcher, Ammon, DeShong (BIB11) 1995; 117 Cortese, Heck (BIB14) 1978; 43 Fleming (BIB5) 1994 9473; Boudjouk, P.; Choi, S.-B.; Hauck, B. J.; Rajkumar, A. B. 3951; Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. The amount of catalyst is based on copper for 1/6[CuH(PPh Mukaiyama, Banno, Narasaka (BIB7) 1974; 96 5237. 2585; Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. 5677; Stryker, J. M., Mahoney, W. S., Daeuble, J. F., Brestensky, D. M. In This sample still contains unknown impurities, one of which may be triphenylphosphine oxide, possibly the major contaminant in the Aldrich samples. This material can be removed by an additional recrystallization, although this was unnecessary for our purposes; Stryker, J. M. Personal communication. Curiously, all attempts at conjugate reduction of an α,β-unsaturated ester or lactone (e.g. methyl cinnamate and coumarin) were fruitless, as no reaction was observed irrespective of catalyst amount or silyl hydride. see Chiu, P.; Chen, B.; Cheng, K.F. ] For representative methods, see Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Meneses, R. 1663; Ikeno, T.; Kimura, T.; Ohtsuka, Y.; Yamada, T. 96; Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. Mori, Fujita, Kajiro, Nishihara, Hiyama (BIB6) 1999; 55 8818; Brestensky, D. M.; Stryker, J. M. 5678. Lipshutz, Keith, Papa, Vivian (BIB2) 1998; 39 9229. See also Kiyooka, S.; Shimizu, A.; Torii, S. , Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. . Chapdelaine, Hulce (BIB10) 1990; 38 3529; Evans, D.A.; Fu, G.C. Pascoe, W. E., Ed.; Marcel Dekker: New York, 1992; pp 29–44. Heathcock, Davidsen, Hug, Flippin (BIB9) 1986; 51 291; See also Mahoney, W. S.; Stryker, J. M. For an example of an intramolecular conjugate reduction/aldol sequence of reactions with stoichiometric [CuH(PPh 8887; Ravasio, N.; Antenori, M.; Gargano, M.; Mastrorilli, P. MUKAIYAMA, T (WOS:A1974U787700020) 1974; 96 EVANS, DA (WOS:A1990EF32200007) 1990; 55 HEATHCOCK, CH (WOS:A1986D406300034) 1986; 51 Ito, H (WOS:A1997YK20700030) 1997; 38 Kiyooka, S (WOS:000074413600030) 1998; 39 CHAPDELAINE MJ (WOS:000086836300007.5) 1990; 38 BRESTENSKY, DM (WOS:A1989AY50100001) 1989; 30 Miura, K (WOS:000072999900041) 1998; 39 MAHONEY, WS (WOS:A1989CB49900008) 1989; 111 FLEMING I (WOS:000086836300007.9) 1994 PILCHER, AS (WOS:A1995QX56800025) 1995; 117 STRYKER JM (WOS:000086836300007.23) Lipshutz, BH (WOS:000074145300011) 1998; 39 CORTESE, NA (WOS:A1978FR28500048) 1978; 43 Boudjouk, P (WOS:000073699300018) 1998; 39 MAHONEY, WS (WOS:A1988L760000048) 1988; 110 Ravasio, N (WOS:A1996UL79200033) 1996; 37 Ikeno, T (WOS:000078816600029) 1999 Chiu, P (WOS:000077192100033) 1998; 39 Barrero, AF (WOS:000083564700045) 1999 Mori, A (WOS:000079625500004) 1999; 55 Appella, DH (WOS:000083166400034) 1999; 121 STRYKER JM (WOS:000086836300007.22) 1992 10.1016/S0040-4020(00)00132-0_BIB8 Fleming (10.1016/S0040-4020(00)00132-0_BIB5) 1994 Pilcher (10.1016/S0040-4020(00)00132-0_BIB11) 1995; 117 10.1016/S0040-4020(00)00132-0_BIB4 Mori (10.1016/S0040-4020(00)00132-0_BIB6) 1999; 55 Heathcock (10.1016/S0040-4020(00)00132-0_BIB9) 1986; 51 10.1016/S0040-4020(00)00132-0_BIB3 Mukaiyama (10.1016/S0040-4020(00)00132-0_BIB7) 1974; 96 10.1016/S0040-4020(00)00132-0_BIB1 10.1016/S0040-4020(00)00132-0_BIB12 Lipshutz (10.1016/S0040-4020(00)00132-0_BIB2) 1998; 39 10.1016/S0040-4020(00)00132-0_BIB13 Chapdelaine (10.1016/S0040-4020(00)00132-0_BIB10) 1990; 38 Cortese (10.1016/S0040-4020(00)00132-0_BIB14) 1978; 43 |
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| Snippet | Exposure of an enone to a catalytic quantity of [CuH(PPh
3)]
6 in the presence of one of several silyl hydrides (PhMe
2SiH, PMHS, HMe
2SiOSiMe
2H) leads to... Exposure of an enone to a catalytic quantity of [CuH(PPh3)](6) in the presence of one of several silyl hydrides (PhMe2SiH, PMHS, HMe2SiOSiMe2H) leads to... |
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| SubjectTerms | Chemistry Chemistry, Organic conjugate reduction copper hydride Physical Sciences Science & Technology silyl hydrides |
| Title | Copper Hydride- Catalyzed Tandem 1,4-Reduction/Alkylation Reactions |
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