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

doi:10.1016/S0957-4166(00)00330-X

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

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-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 language	English
Pages (from-to)	3481-3493
Number of pages	13
Journal	Tetrahedron Asymmetry
Volume	11
Issue number	17
DOIs	https://doi.org/10.1016/S0957-4166(00)00330-X
Publication status	Published - 8 Sept 2000
Externally published	Yes

Keywords

Alpha-sulfinyl alcohols
Beta-hydroxy sulfoxides
Pm3-mo calculations
Ab-initio
Parameters

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10.1016/S0957-4166(00)00330-X

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@article{8c74daf0ddac42509f4f3ecfde4543db,

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

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.",

keywords = "Alpha-sulfinyl alcohols, Beta-hydroxy sulfoxides, Pm3-mo calculations, Ab-initio, Parameters",

author = "Gregorio Asensio and Pablo Gavia and Ana Cuenca and {De Arellano}, {M. Carmen Ram{\'i}rez} and Domingo, {Luis R.} and Mercedes Medio-Sim{\'o}n",

note = "Funding Information: We thank the Direcci{\'o}n General de Ense{\~n}anza Superior (PB96-0757) and the Generalitat Valenciana (GVDOC99-22-2) for financial support. Additional thanks go to the Generalitat Valenciana for a grant (A.C.).",

year = "2000",

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doi = "10.1016/S0957-4166(00)00330-X",

language = "English",

volume = "11",

pages = "3481--3493",

journal = "Tetrahedron Asymmetry",

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TY - JOUR

T1 - First synthesis of the chiral mixed O/S ligands, 1,2-sulfinyl thiols

T2 - Application as chiral proton sources in enantioselective protonations of enolates

AU - Asensio, Gregorio

AU - Gavia, Pablo

AU - Cuenca, Ana

AU - De Arellano, M. Carmen Ramírez

AU - Domingo, Luis R.

AU - Medio-Simón, Mercedes

N1 - Funding Information: We thank the Dirección General de Enseñanza Superior (PB96-0757) and the Generalitat Valenciana (GVDOC99-22-2) for financial support. Additional thanks go to the Generalitat Valenciana for a grant (A.C.).

PY - 2000/9/8

Y1 - 2000/9/8

N2 - 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.

AB - 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.

KW - Alpha-sulfinyl alcohols

KW - Beta-hydroxy sulfoxides

KW - Pm3-mo calculations

KW - Ab-initio

KW - Parameters

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DO - 10.1016/S0957-4166(00)00330-X

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SN - 0957-4166

VL - 11

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 17

ER -

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

Abstract

Keywords

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