Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 10, Pages 3188-3192Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812836
Keywords
allylic epoxide; boron; copper; cyclopropane; cyclopropylboronate
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Funding
- European Research Council [ERC-337776]
- MINECO [CTQ2016-78779-R]
- Universita degli Studi di Roma La Sapienza
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Herein, we report a catalytic and stereospecific method for the preparation of enantioenriched alpha-hydroxy cyclopropylboronates with control in four contiguous stereocenters. The reaction involves the borylation of readily available allylic epoxides using an inexpensive Cu(I) salt and a commercially available phosphine ligand. High diastereocontrol is achieved and different diastereomers can be selectively prepared. Functionalization of the carbon-boron bond provides access to different enantiomerically enriched trisubstituted cyclopropanes from a common intermediate.
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