Acyclic stereoselection. 46. Stereochemistry of the Michael addition of N, N-disubstituted amide and thioamide enolates to. alpha.,. beta.-unsaturated ketones

DA Oare, MA Henderson, MA Sanner…

Index: Oare, David A.; Henderson, Mark A.; Sanner, Mark A.; Heathcock, Clayton H. Journal of Organic Chemistry, 1990 , vol. 55, # 1 p. 132 - 157

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Abstract

Background The Michael addition reaction is a powerful and widely used method of synthesis. 2 Although the reaction was discovered3 and developed as a general method4 more than 100 years ago, its stereochemistry has been investigated only re~ ently.~ Several years ago, in the context of an alkaloid total synthesis? we discovered that lactam 1 adds cleanly to 6-methylhept-2-en-4-one to provide keto lactam 2 as a 9: l mixture of isomers ( ...