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Synthesis 2009(5): 853-859  
DOI: 10.1055/s-0028-1083368
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Homoallylic Alcohols via Lewis Acid Assisted Enantioselective Desymmetrization

Bing Yu, Frederic Menard, Naohiro Isono, Mark Lautens*
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada
Fax: +1(416)9468185; e-Mail: mlautens@chem.utoronto.ca;
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Publication History

Received 30 October 2008
Publication Date:
11 February 2009 (online)

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Abstract

A highly enantioselective allylic substitution of (Z)-but-2-ene-1,4-diol derivatives was developed using a rhodium(I) catalyst and arylboronic acids as nucleophiles. The reaction yields versatile homoallylic alcohols from readily available linear biscarbonates.

Key words

homoallylic alcohols - rhodium - boronic acids - desymmetrization - asymmetric allylic substitution

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P-Phos is stable to air in the solid state; however, it is highly sensitive to oxygen once in solution.