Enantioselective Three-Step Synthesis of Homo-β-proline: A Donor–Acceptor Cyclopropane as Key Intermediate

An enantioselective three-step synthesis of the GABA uptake inhibitor (S)-(+)-homo-β-proline was developed. The basis for the synthesis was the enantioselective CuI-catalyzed cyclopropanation of N-Boc-pyrrole, a substrate that persistently has proved to be challenging in such transformations. The cy...

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Bibliographic Details
Published in:Organic letters 2017-05, Vol.19 (10), p.2754-2757
Main Authors: Pilsl, Ludwig K. A, Ertl, Thomas, Reiser, Oliver
Format: Article
Language:English
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Summary:An enantioselective three-step synthesis of the GABA uptake inhibitor (S)-(+)-homo-β-proline was developed. The basis for the synthesis was the enantioselective CuI-catalyzed cyclopropanation of N-Boc-pyrrole, a substrate that persistently has proved to be challenging in such transformations. The cyclopropanation can be performed on a 150 mmol scale, and the two subsequent steps (i.e., hydrogenation and in situ cyclopropane-opening/double-deprotection) toward the target molecule proceed smoothly in quantitative yield without loss of enantiopurity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01111