Remote stereocontrol in the synthesis of acyclic 1,4-diols and 1,4-aminoalcohols from 2-sulfinyl dienes.

Abstract

The highly diastereoselective conjugate addition of alcohols and amines (RXH) to enantiopure 2-sulfinyl dienes renders transient allylic sulfoxides which undergo sulfoxide-sulfenate rearrangement and sulfenate cleavage providing 2-ene-1,4-diols and 2-ene-1,4-aminoalcohols with up to 99:1 dr. The method allows for the generation of two stereocenters in a single synthetic operation with remote chirality transfer of one center into the other.

DOI: 10.1021/ol502592y

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Cite this paper

@article{Pradilla2014RemoteSI, title={Remote stereocontrol in the synthesis of acyclic 1,4-diols and 1,4-aminoalcohols from 2-sulfinyl dienes.}, author={Roberto F{\'e}rnandez de la Pradilla and Marina Velado and Ignacio Colomer and Carmen Simal and Alma Viso and Heinz Gornitzka and Catherine Hemmert}, journal={Organic letters}, year={2014}, volume={16 19}, pages={5200-3} }