Stereochemistry of cuprate addition to 4-, 5-, and 6-alkylcycloheptenones

CH Heathcock, TC Germroth…

Index: Heathcock,C.H. et al. Journal of Organic Chemistry, 1979 , vol. 44, p. 4481 - 4487

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Citation Number: 19

Abstract

The reactions of cycloheptenones 1-7 with MezCuLi and (tB &CuLi have been studied. Stereostructures of the resulting diastereomeric products have been determined by comparison with known compounds, by unambiguous synthesis, or by the use of 13C NMR spectroscopy. Good stereoselectivity is observed in the reaction of MezCuLi with enones 2, 4, and 7 and in the reaction of (tB &CuLi with enones 1, 5, and 6.