Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 82, Pages 10799-10802Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc04058h
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Funding
- Auburn University
- National Science Foundation [CHE-2042353]
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A highly stereoselective synthesis of (E)-delta-boryl-anti-homoallylic alcohols has been developed in good yields with excellent E-selectivity. The E-vinylboronate group in the products provides a useful handle for cross-coupling reactions, as illustrated in the fragment synthesis of chaxamycins.
A highly stereoselective synthesis of (E)-delta-boryl-anti-homoallylic alcohols is developed. In the presence of a Lewis acid, aldehyde allylation with alpha-boryl-(E)-crotylboronate gave delta-boryl-anti-homoallylic alcohols in good yields with excellent E-selectivity. The E-vinylboronate group in the products provides a useful handle for cross-coupling reactions as illustrated in the fragment synthesis of chaxamycins.
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