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O-nitroso aldol synthesis: Catalytic enantioselective route to alpha-aminooxy carbonyl compounds via enamine intermediate.

ABSTRACT: The approach using pyrrolidine enamine as substrate has been studied for this synthesis, and an important catalyst structural feature has been developed. After survey of pyrrolidine-based Brønsted acid catalyst, tetrazole catalyst (3f) was found to be optimal in synthesis of aminooxy carbonyl compounds in high yields, with complete enantioselectivity not only for aldehydes but also for ketones.

SUBMITTER: Momiyama N

PROVIDER: S-EPMC397388 | biostudies-literature | 2004 Apr

REPOSITORIES: biostudies-literature

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O-nitroso aldol synthesis: Catalytic enantioselective route to alpha-aminooxy carbonyl compounds via enamine intermediate.

Momiyama Norie N Torii Hiromi H Saito Susumu S Yamamoto Hisashi H

Proceedings of the National Academy of Sciences of the United States of America 20040405 15

The approach using pyrrolidine enamine as substrate has been studied for this synthesis, and an important catalyst structural feature has been developed. After survey of pyrrolidine-based Brønsted acid catalyst, tetrazole catalyst (3f) was found to be optimal in synthesis of aminooxy carbonyl compounds in high yields, with complete enantioselectivity not only for aldehydes but also for ketones. ...[more]

PMID: 15067138

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