First synthesis of the chiral mixed O/S ligands, 1,2-sulfinyl thiols: Application as chiral proton sources in enantioselective protonations of enolates

Gregorio Asensio, Pablo Gavia, Ana Cuenca, M. Carmen Ramírez De Arellano, Luis R. Domingo, Mercedes Medio-Simón

Research output: Indexed journal article Articlepeer-review

14 Citations (Scopus)

Abstract

A suitable method for the preparation of the chiral mixed O/S ligands 1,2-sulfinyl thiols is described. These compounds have then been used as a chiral proton source in the enantioselective protonation of 2-methyl tetralone enolate and the results are compared with those obtained from the analogous alcohols. A theoretical model is proposed to explain the different behaviors exhibited in the protonation reaction for each of these proton sources. Configurational assignments for the new chiral thiols have been carried out by means of X-ray analysis. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)3481-3493
Number of pages13
JournalTetrahedron Asymmetry
Volume11
Issue number17
DOIs
Publication statusPublished - 8 Sept 2000
Externally publishedYes

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