期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 3, 页码 1040-1043出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja512124c
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资金
- NIH-NIGMS [R01GM080269]
- Amgen
- Gordon and Betty Moore Foundation
- Caltech Center for Catalysis and Chemical Synthesis
- Caltech
- Toray Industries Inc.
- NSF
- Japan Society for the Promotion of Science
A catalytic enantioselective method for the synthesis of alpha-quaternary Mannich-type products is reported. The two-step sequence of (1) Mannich reaction followed by (2) decarboxylative enantioselective allylic alkylation serves as a novel strategy to in effect access asymmetric Mannich-type products of thermodynamic enolates of substrates possessing additional enolizable positions and acidic protons. Palladium-catalyzed decarboxylative allylic alkylation enables the enantioselective synthesis of five-, six-, and seven-membered ketone, lactam, and other heterocyclic systems. The mild reaction conditions are notable given the acidic free NH groups and high functional group tolerance in each of the substrates. The utility of this method is highlighted in the first total synthesis of (+)-sibirinine.
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