Journal of Organic Chemistry p. 5049 - 5051 (1992)
Update date:2022-08-04
Topics:
Shida, Naomi
Uyehara, Tadao
Yamamoto, Yoshinori
Di-(-)-menthyl nona-2,7-diene-1,9-dioate (1) is converted to (-)-menthyl 3(S)-(N-benzylamino)-2(S)-(-)-menthoxycarbonyl-1(S)-cyclohexane-1-acetate (2) with high diastereoselectivity upon treatment with the amide cuprate or zincate reagent Bn(TMS)NMLn in the presence of ZnCl2.The folded orientation of the two enoate moieties of 1 is essential for this high asymmetric cyclization via tandem conjugate addition.
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