期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 25, 页码 8805-8814出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja808811u
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资金
- NSF [CHE-0348979]
- PRF
- Elizabeth Tuckerman Foundation
- Northwestern University
- Abbott Laboratories
- Amgen
- AstraZeneca
- GlaxoSmithKline
- Boehringer-Ingelheim
- Alfred P. Sloan Foundation
- American Cancer Society Research
The synthesis of beta-hydroxy carbonyl compounds is an. important goal due to their prevalence in bioactive molecules. A novel approach to construct these structural motifs involves the multicomponent reaction of acylsilanes, amides, and electrophiles. The addition of amide enolates to acylsilanes; generates beta-silyloxy homoenolate reactivity by undergoing a 1,2-Brook rearrangement. These unique nucleophiles formed in situ can then undergo addition to alkyl halides, aldehydes, ketones, and imines. The gamma-amino-beta-hydroxy amide products derived from the addition of these homoenolates to N-diphenylphosphinyl imines are generated with excellent diastereoselectivity (>= 20:1) and can be efficiently converted to highly valuable gamma-lactams. Finally, the use of optically active amide enolates delivers beta-hydroxy amide products with high levels of diastereoselectivity (>= 10:1).
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