Two enantiomeric five-membered ring building blocks from the same educt: This was achieved by reaction of 1 with two different nucleophilic reagents. 1,4-Addition of R2CuLi to 1 and cleavage of MeOH furnished (R,R)-2; 1,2-Addition of RM to 1, allyl rearrangement, and MeOH-cleavage lead to the mirror image (S,S)-2.
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Bestmann et al. (1986) studied this question.
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