期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 46, 页码 15621-15625出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b10288
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资金
- National Institutes of Health [GM R35 127010]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM045532, R01GM030938, R01GM063167] Funding Source: NIH RePORTER
A catalytic, enantioselective method for the preparation of chiral, non-racemic, alkylboronic esters bearing two vicinal stereogenic centers is described. The reaction proceeds via a 1,2-migration of a zwitterionic thiiranium-boronate complex to give exclusively anti carbosulfenylation products. A broad scope of aryl groups migrate with good yield and excellent enantioselectivity (up to 99:1 e.r.). Similarly, a range of di- and trisubstituted alkenylboronic esters are competent reaction partners. This method provides access to both secondary and tertiary chiral alkylboronic esters.
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