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Asymmetric Synthesis of α,γ‐Substituted γ‐Sultones via Allylation of Chiral Lithiated Sulfonates
Author(s) -
Enders Dieter,
Harnying Wacharee,
Vignola Nicola
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300342
Subject(s) - enantiopure drug , chemistry , chiral auxiliary , epimer , enantiomer , enantioselective synthesis , stereochemistry , organic chemistry , asymmetric induction , catalysis
The first auxiliary controlled asymmetric synthesis of enantiopure α,γ‐substituted γ‐sultones via α‐allylation of lithiated sulfonates by using 1,2:5,6‐di‐ O ‐isopropylidene‐α‐ D ‐allofuranose as chiral auxiliary is described. The high asymmetric inductions of the α‐allylations were reached in good to excellent yields. Successive epimerization‐free cleavage of the auxiliary and diastereoselective ring closure of the sulfonic acid intermediates in a one‐pot procedure led to the title compounds in good to excellent yields and diastereo‐ and enantiomeric excesses ( de , ee ≥ 98%). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)