Journal
SYNLETT
Volume -, Issue 16, Pages 2518-2522Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2008-1078235
Keywords
atropisomerism; amides; asymmetric synthesis; alkaloids; planar chirality
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- The Asahi Glass Foundation
- The Naito Foundation
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An efficient approach to nine-membered diallylic cyclic amides having a variety of substituents has been developed. The synthesized amides have stable planar chirality at ambient temperature. The transformation of the enantiomerically enriched amides provides optically active compounds containing stereogenic centers in a stereospecific fashion. As a demonstration of the synthetic utility of the amides, we have synthesized (+)-gamma-lycorane using such an optically active amide as a chiral building block.
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