Bulky, Optically Active P-Stereogenic Phosphine–Boranes from Pure H-Menthylphosphinates

Bulky, Optically Active P-Stereogenic Phosphine–Boranes from Pure H-Menthylphosphinates

The transformation of readily available pure-H-menthylphosphinates into chiral phosphinous acid-boranes permits the elaboration of bulky P-stereogenic secondary phosphine–boranes. Taking advantage of the synthetic potential of these compounds, a broad range of hindered P-chiral tertiary phosphine–bo...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 133; no. 28; pp. 10728 - 10731
Main Authors: Gatineau, David, Giordano, Laurent, Buono, Gérard
Format: Journal Article
Language:English
Published: United States American Chemical Society 20-07-2011
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Summary:The transformation of readily available pure-H-menthylphosphinates into chiral phosphinous acid-boranes permits the elaboration of bulky P-stereogenic secondary phosphine–boranes. Taking advantage of the synthetic potential of these compounds, a broad range of hindered P-chiral tertiary phosphine–boranes has been prepared with excellent enantiomeric excesses. The utility of bulky o-tolylphosphines was illustrated by the synthesis of a rare enantiopure phosphapalladacycle (S P,S P)-12.
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja2034816