Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones

José L. García Ruano; David Barros; M. Carmen Maestro; Ana M. Martín Castro; Paul R. Raithby

doi:10.1016/S0957-4166(00)00407-9

Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones

José L. García Ruano
, David Barros
, M. Carmen Maestro
, Ana M. Martín Castro
, Paul R. Raithby

Department of Chemistry

Universidad Autónoma de Madrid
University of Cambridge

Research output: Contribution to journal › Article › peer-review

8 Citations (SciVal)

Abstract

We describe the addition reactions of α-thiocarbanions derived from sulfoxides, thioethers, and sulfones to 2-(p-tolylsulfinyl)cyclohexanones. The high stereoselectivity observed in the formation of the chiral hydroxylic carbon is controlled by the configuration of the sulfinyl group at the substrate, but it is modulated by the nature of the sulfur function at the reagent (SOTol>SO₂Ph>SPh). The highly stereoselective formation of the second stereogenic center generated in these reactions from prochiral anions is only achieved with sulfinylcarbanions, the configuration of which controls that of such a center. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	4385-4395
Number of pages	11
Journal	Tetrahedron Asymmetry
Volume	11
Issue number	21
DOIs	https://doi.org/10.1016/S0957-4166(00)00407-9
Publication status	Published - 3 Nov 2000

Funding

The authors would like to thank the Dirección General de Investigación Cientı́fica y Técnica for financial support (PB 98-0102).

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/S0957-4166(00)00407-9

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title = "Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones",

abstract = "We describe the addition reactions of α-thiocarbanions derived from sulfoxides, thioethers, and sulfones to 2-(p-tolylsulfinyl)cyclohexanones. The high stereoselectivity observed in the formation of the chiral hydroxylic carbon is controlled by the configuration of the sulfinyl group at the substrate, but it is modulated by the nature of the sulfur function at the reagent (SOTol>SO2Ph>SPh). The highly stereoselective formation of the second stereogenic center generated in these reactions from prochiral anions is only achieved with sulfinylcarbanions, the configuration of which controls that of such a center. (C) 2000 Elsevier Science Ltd.",

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doi = "10.1016/S0957-4166(00)00407-9",

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T1 - Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones

AU - García Ruano, José L.

AU - Barros, David

AU - Maestro, M. Carmen

AU - Martín Castro, Ana M.

AU - Raithby, Paul R.

PY - 2000/11/3

Y1 - 2000/11/3

N2 - We describe the addition reactions of α-thiocarbanions derived from sulfoxides, thioethers, and sulfones to 2-(p-tolylsulfinyl)cyclohexanones. The high stereoselectivity observed in the formation of the chiral hydroxylic carbon is controlled by the configuration of the sulfinyl group at the substrate, but it is modulated by the nature of the sulfur function at the reagent (SOTol>SO2Ph>SPh). The highly stereoselective formation of the second stereogenic center generated in these reactions from prochiral anions is only achieved with sulfinylcarbanions, the configuration of which controls that of such a center. (C) 2000 Elsevier Science Ltd.

AB - We describe the addition reactions of α-thiocarbanions derived from sulfoxides, thioethers, and sulfones to 2-(p-tolylsulfinyl)cyclohexanones. The high stereoselectivity observed in the formation of the chiral hydroxylic carbon is controlled by the configuration of the sulfinyl group at the substrate, but it is modulated by the nature of the sulfur function at the reagent (SOTol>SO2Ph>SPh). The highly stereoselective formation of the second stereogenic center generated in these reactions from prochiral anions is only achieved with sulfinylcarbanions, the configuration of which controls that of such a center. (C) 2000 Elsevier Science Ltd.

UR - https://www.scopus.com/pages/publications/0034601958

U2 - 10.1016/S0957-4166(00)00407-9

DO - 10.1016/S0957-4166(00)00407-9

M3 - Article

AN - SCOPUS:0034601958

SN - 0957-4166

VL - 11

SP - 4385

EP - 4395

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 21

ER -

Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones

Abstract

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