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. 2011 May 6;13(9):2468-71.
doi: 10.1021/ol200718y. Epub 2011 Apr 6.

Enantiopure 1,4-diols and 1,4-aminoalcohols via stereoselective acyclic sulfoxide-sulfenate rearrangement

Roberto Fernández de la Pradilla  1 , Ignacio Colomer, Mercedes Ureña, Alma Viso
Affiliations

Enantiopure 1,4-diols and 1,4-aminoalcohols via stereoselective acyclic sulfoxide-sulfenate rearrangement

Roberto Fernández de la Pradilla et al. Org Lett. .

Abstract

Treatment of acyclic α-hydroxy and α-tosylamino sulfinyl dienes with amines affords enantiopure 1,4-diol or 1,4-hydroxysulfonamide derivatives in good yields and diastereoselectivities. This one-pot procedure entails a conjugate addition that triggers a diastereoselective sulfoxide-sulfenate [2,3]-sigmatropic rearrangement.

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