期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 7, 页码 3246-3251出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo202679u
关键词
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资金
- National Institute of General Medical Sciences [R01 GM084927]
- Novartis
Silyl glyoxylates react with enolates and enones to afford either glycolate aldol or Michael adducts. Product identity is controlled by the countercation associated with the enolate. Reformatsky nucleophiles in the presence of additional Zn(OTf)(2) result in aldol coupling (A), while lithium enolates provide the Michael coupling (B). Deprotonation of the aldol product A with LDA induces equilibration to form the minor diastereomer of Michael product B. This observation suggests that formation of the major diastereomer of Michael product B does not occur via an aldol/retro-aldol/Michael sequence.
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