期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 24, 页码 7136-7139出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201803472
关键词
atropisomerism; biaryls; esters; organomagnesium reagents; stereoselectivity
资金
- Swiss National Science Foundation [BSSGI0-155902/1]
- University of Basel
- NCCR Molecular Systems Engineering
- Swiss National Science Foundation (SNF) [BSSGI0_155902] Funding Source: Swiss National Science Foundation (SNF)
A strategy for the remote central-to-axial chirality conversion by simultaneous planarization of an encoding and a transient stereocenter is presented. Based on a diastereoselective double addition of a chiral 1,5-bifunctional organomagnesium alkoxide reagent to a broad range of aryl ester substrates, axially chiral biaryls are directly obtained upon in situ reduction. Various structurally distinct atropisomeric biaryl silanes that serve as valuable chiral biaryl anion surrogates are accessible in one step with e.r.values of up to 98:2.
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