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Phosphine-catalyzed asymmetric additions of malonate esters to {gamma}-substituted allenoates and allenamides.

ABSTRACT: Because carbonyl groups are ubiquitous in organic chemistry, the ability to synthesize functionalized carbonyl compounds, particularly enantioselectively, is an important objective. We have developed a straightforward and versatile method for catalytic asymmetric carbon-carbon bond formation at the ?-position of carbonyl compounds, specifically, phosphine-catalyzed additions of malonate esters to ?-substituted allenoates and allenamides. Mechanistic studies have provided insight into the reaction pathway.

SUBMITTER: Sinisi R

PROVIDER: S-EPMC2996437 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Phosphine-catalyzed asymmetric additions of malonate esters to {gamma}-substituted allenoates and allenamides.

Sinisi Riccardo R Sun Jianwei J Fu Gregory C GC

Proceedings of the National Academy of Sciences of the United States of America 20100712 48

Because carbonyl groups are ubiquitous in organic chemistry, the ability to synthesize functionalized carbonyl compounds, particularly enantioselectively, is an important objective. We have developed a straightforward and versatile method for catalytic asymmetric carbon-carbon bond formation at the γ-position of carbonyl compounds, specifically, phosphine-catalyzed additions of malonate esters to γ-substituted allenoates and allenamides. Mechanistic studies have provided insight into the reactio ...[more]

PMID: 20624987

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