Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 29, Pages 7619-7623Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404072
Keywords
carbocycles; cyclization; diastereoselectivity; organocatalysis; synthetic methods
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Funding
- Welch Foundation [AX-1593]
- NSF [CHE 0909954]
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A highly diastereodivergent synthesis of tetrasubstituted cyclohexanes has been achieved using modularly designed organocatalysts (MDOs) which are self-assembled in situ from amino acids and cinchona alkaloid derivatives. Diastereodivergence is realized through controlling the stereoselectivity of the individual steps of a tandem Michael/Michael reaction. Up to 8 of the 16 possible stereoisomers have been successfully obtained in high stereoselectivities using MDOs for the tandem reaction and an ensuing epimerization. The method was used in the enantioselective synthesis of the natural products (-)-alpha- and beta-lycoranes.
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