Diastereodivergent Synthesis of 2-Ene-1,4-hydroxy Sulfides from 2-Sulfinyl Dienes via Tandem Sulfa-Michael/Sulfoxide-Sulfenate Rearrangement

descriptionPublicationkeyboard_double_arrow_right Article 10 Dec 2020 English Publisher:American Chemical Society (ACS)Journal:Organic Letters, volume 23, pages 202-206 (issn: 1523-7060, eissn: 1523-7052,

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Authors: Marina Velado; Roberto Fernández de la Pradilla; Alma Viso;

doi: 10.1021/acs.orglett.0c03929

pmid: 33300806

handle: 10261/232257

Diastereodivergent Synthesis of 2-Ene-1,4-hydroxy Sulfides from 2-Sulfinyl Dienes via Tandem Sulfa-Michael/Sulfoxide-Sulfenate Rearrangement

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Abstract

The highly diastereoselective sulfa-Michael addition of thiolates to enantiopure 2-sulfinyl dienes leads to anti or syn 2-ene-1,4-hydroxy sulfides in good yields and selectivities dependent on the reaction conditions in a diastereodivergent process. Synthetic applications of these enantiopure hydroxy sulfides by subsequent sigmatropic rearrangements have been outlined.

Related Organizations

Instituto de Química Orgánica General
Spain
Spanish National Research Council
Spain

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