Tetrahedron letters

SmI 2-promoted conjugate reduction of α, β-unsaturated esters and ketones studied in comparison with Mukaiyama-Michael reaction of ketene silyl acetal

Y Fujita, S Fukuzumi, J Otera

Index: Fujita, Yukihiro; Fukuzumi, Shunichi; Otera, Junzo Tetrahedron Letters, 1997 , vol. 38, # 12 p. 2121 - 2124

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Citation Number: 21

Abstract

SmI2-promoted conjugate reduction of α, β-unsaturated esters and ketones proceeds in a manner quite similar to Mukaiyama-Michael reaction of ketene silyl acetal. The more substituted esters are reduced more preferentially than the less substituted ones. The substrates with a 12 or 16 membered-ring structure undergo reduction smoothly. On the other hand, the 6-membered substrates completely fail to react under the same conditions. ...