The first enantiomerically pure synthesis of (2S,1′S)-(cyclopent-2-enyl)glycine by boron trifluoride mediated asymmetric 1,3-diploar cycloaddition
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 18,p. 2137-2138
- https://doi.org/10.1039/cc9960002137
Abstract
Chiral spiro nitrone 3, treated with (3-trimethylsilyl)cyclopent-1-ene in the presence of BF3.Et2O, gives the 1,3-diploar cycloadduct 4 as a single isomer, which converted to (2S,1′S)-(cyclopent-2-enyl)glycine (2S,1′S)-7 by alkaline hydrolysis, catalytic reduction and BF3 mediated alkene formation.Keywords
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