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

Org Lett

Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.

Published: January 2021

AI Article Synopsis

  • The sulfa-Michael addition process allows thiolates to react with enantiopure 2-sulfinyl dienes, producing 2-ene-1,4-hydroxy sulfides with high diastereoselectivity.
  • The yields and selectivities of the reactions can be influenced by varying the reaction conditions, showcasing a diastereodivergent outcome.
  • Additionally, these enantiopure hydroxy sulfides can be further utilized in synthetic applications through sigmatropic rearrangements.

Article Abstract

The highly diastereoselective sulfa-Michael addition of thiolates to enantiopure 2-sulfinyl dienes leads to or 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.

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Source
http://dx.doi.org/10.1021/acs.orglett.0c03929DOI Listing

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