Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 128, Issue 20, Pages 6745-6754Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja060812g
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Funding
- NIGMS NIH HHS [R01 GM033049, R01 GM033049-30A1, GM33049] Funding Source: Medline
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An atom economic, selective, and highly practical two- metal one- pot synthesis of heterocycles has been developed that efficiently affords enantio- and diastereopure N- and O- heterocyclic products. Furthermore, use of a chiral catalyst in the two- metal procedure allows formation of all possible diastereomers, even those that are traditionally difficult to access via cyclization routes due to thermodynamics. Interestingly, the nature of the enantiodiscriminating event differs between the use of amine versus alcohol nucleophiles. The method also affords heterocyclic products that are synthetically useful intermediates. Through the Z- vinylsilane a variety of stereodefined trisubstituted olefin products can be accessed including several all- carbon motifs. Finally, the utility of these heterocyclic products in total synthesis is demonstrated through concise syntheses of a kainoid intermediate, a constituent of oil of rose, and the ring B portion of bryostatin, a potent chemotherapeutic.
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