Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 16, Pages 5763-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja901283q
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Funding
- NSF [CHE-0749566]
- NIH/NCI [CA047148]
- NIH/NIGMS [GM007598-30]
- Kwanjeong Educational Foundation Fellowship
- Eli Lilly Organic Chemistry Fellowship
- Merck Co., Inc.
- Harvard College Research Program
- Pfizer Inc.
- Amgen
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0749566] Funding Source: National Science Foundation
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We describe a synthetic sequence that allows for the preparation of optically active trans-1,2-diol monosilyl ether derivatives from ketones, providing a new means for retrosynthetic simplification of differentiated diol and polyol targets. The sequence involves silyl enol ether formation, Shi asymmetric epoxidation, and then regio- and stereospecific addition of hydride, methide, or higher alkylide. The tactical combination presented has not been integrated in synthetic problem solving, so far as we are aware, but has promise for broad application.
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