期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 16, 页码 4186-4190出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310380
关键词
1; 6-addition; asymmetric catalysis; boron; copper; enantioselectivity
资金
- ERC [258580]
- EPSRC
- Pfizer
- AstraZeneca
- University of Edinburgh
- European Research Council (ERC) [258580] Funding Source: European Research Council (ERC)
- Engineering and Physical Sciences Research Council [EP/I004769/2, EP/I004769/1] Funding Source: researchfish
- EPSRC [EP/I004769/2, EP/I004769/1] Funding Source: UKRI
Chiral secondary allylboronates are obtained in high enantioselectivities and 1,6:1,4 ratios by the copper-catalyzed 1,6-boration of electron-deficient dienes with bis(pinacolato)diboron (B-2(pin)(2)). The reactions proceed efficiently using catalyst loadings as low as 0.0049mol%. The allylboronates may be oxidized to the allylic alcohols, and can be used in stereoselective aldehyde allylborations. This process was applied to a concise synthesis of atorvastatin, in which the key 1,6-boration was performed using only a 0.02mol% catalyst loading.
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