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Short Communication
Enantioselective Synthesis of (R)-Homoboroproline from (S)-Proline Using a Borylation Approach
Article first published online: 25 JUN 2012
DOI: 10.1002/ejoc.201200652
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Georgiou, I. and Whiting, A. (2012), Enantioselective Synthesis of (R)-Homoboroproline from (S)-Proline Using a Borylation Approach. Eur. J. Org. Chem., 2012: 4110–4113. doi: 10.1002/ejoc.201200652
Publication History
- Issue published online: 23 JUL 2012
- Article first published online: 25 JUN 2012
- Manuscript Received: 15 MAY 2012
Funded by
- One North East
- Department of Chemistry at Durham University
Keywords:
- Aldol reactions;
- Boron;
- Enantioselectivity;
- Amino acids;
- Asymmetric synthesis
Abstract
(S)-Proline was converted through a five-step sequence into (R)-homoboroproline hydrochloride in 29 % overall yield with 97 % ee The key step was the conversion of N-Boc iodomethylpyrrolidine into the corresponding pinacol boronate ester by an efficient copper(I)-catalyzed borylation reaction by using bispinacolatodiboron.