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Synthesis 2007(12): 1837-1840
DOI: 10.1055/s-2007-983719
DOI: 10.1055/s-2007-983719
PAPER
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Synthesis of α-Phenyl-γ-Hetero-Substituted Isopropyl Sulfonates via Diastereoselective Ring-Opening of γ-Sultones
Further Information
Received
2 April 2007
Publication Date:
08 June 2007 (online)
Publication History
Publication Date:
08 June 2007 (online)
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Abstract
An efficient route to α-phenyl-γ-hetero (O, S, Se, Cl)-substituted isopropyl sulfonates via SN2-ring opening of γ-sultones, easily available by asymmetric synthesis from chiral lithiated sulfonates, is described. The title compounds are obtained in very good overall yields of 65-86% over three steps and excellent diastereo- and enantiomeric excesses (de = 94-96%, ee ≥ 98%).
Key words
sultones - sulfonates - asymmetric synthesis - ring-opening - heteronucleophiles
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