Enantioselective protonation/diastereoselective reduction with sodium naphthalenide-acetamide; a new synthesis of chiral trans-2-phenylcyclohexanol

Gregorio Asensio; A. Cuenca; P. Gaviña; Mercedes Medio-Simón

doi:10.1016/S0040-4039(99)00615-2

Enantioselective protonation/diastereoselective reduction with sodium naphthalenide-acetamide; a new synthesis of chiral trans-2-phenylcyclohexanol

Gregorio Asensio^*
, A. Cuenca
, P. Gaviña
, Mercedes Medio-Simón

^*Autor corresponent d’aquest treball

Producció científica: Article en revista indexada › Article › Avaluat per experts

21 Cites (Scopus)

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An efficient synthesis of trans-2-phenylcyclohexanol has been achieved by enantioselective protonation of the enolate of 2-phenylcyclohexanone with α-sulfinyl alcohols and subsequent reduction of the chiral ketone by sodium naphthalenide in the presence of acetamide. Interestingly, the chirality source is not consumed in the synthesis of the chiral target.

Idioma original	Anglès
Pàgines (de-a)	3939-3940
Nombre de pàgines	2
Revista	Tetrahedron Letters
Volum	40
Número	20
DOIs	https://doi.org/10.1016/S0040-4039(99)00615-2
Estat de la publicació	Publicada - 14 de maig 1999
Publicat externament	Sí

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10.1016/S0040-4039(99)00615-2

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title = "Enantioselective protonation/diastereoselective reduction with sodium naphthalenide-acetamide; a new synthesis of chiral trans-2-phenylcyclohexanol",

abstract = "An efficient synthesis of trans-2-phenylcyclohexanol has been achieved by enantioselective protonation of the enolate of 2-phenylcyclohexanone with α-sulfinyl alcohols and subsequent reduction of the chiral ketone by sodium naphthalenide in the presence of acetamide. Interestingly, the chirality source is not consumed in the synthesis of the chiral target.",

keywords = "Alpha-sulfinyl alcohols, Protonation, Alkylation",

author = "Gregorio Asensio and A. Cuenca and P. Gavi{\~n}a and Mercedes Medio-Sim{\'o}n",

note = "Funding Information: Acknowledgements: We thank the Direcci6n General de Ensefianza Superior (PB96-0757) for financial support and the Ministerio de Educaci6n (P.G.) and the Generatitat Valenciana (A.C.) for the grant provided.",

year = "1999",

month = may,

day = "14",

doi = "10.1016/S0040-4039(99)00615-2",

language = "English",

volume = "40",

pages = "3939--3940",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "20",

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TY - JOUR

T1 - Enantioselective protonation/diastereoselective reduction with sodium naphthalenide-acetamide; a new synthesis of chiral trans-2-phenylcyclohexanol

AU - Asensio, Gregorio

AU - Cuenca, A.

AU - Gaviña, P.

AU - Medio-Simón, Mercedes

N1 - Funding Information: Acknowledgements: We thank the Direcci6n General de Ensefianza Superior (PB96-0757) for financial support and the Ministerio de Educaci6n (P.G.) and the Generatitat Valenciana (A.C.) for the grant provided.

PY - 1999/5/14

Y1 - 1999/5/14

N2 - An efficient synthesis of trans-2-phenylcyclohexanol has been achieved by enantioselective protonation of the enolate of 2-phenylcyclohexanone with α-sulfinyl alcohols and subsequent reduction of the chiral ketone by sodium naphthalenide in the presence of acetamide. Interestingly, the chirality source is not consumed in the synthesis of the chiral target.

AB - An efficient synthesis of trans-2-phenylcyclohexanol has been achieved by enantioselective protonation of the enolate of 2-phenylcyclohexanone with α-sulfinyl alcohols and subsequent reduction of the chiral ketone by sodium naphthalenide in the presence of acetamide. Interestingly, the chirality source is not consumed in the synthesis of the chiral target.

KW - Alpha-sulfinyl alcohols

KW - Protonation

KW - Alkylation

UR - https://www.scopus.com/pages/publications/0033553373

UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:000080130600034&DestLinkType=FullRecord&DestApp=WOS_CPL

U2 - 10.1016/S0040-4039(99)00615-2

DO - 10.1016/S0040-4039(99)00615-2

M3 - Article

AN - SCOPUS:0033553373

SN - 0040-4039

VL - 40

SP - 3939

EP - 3940

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 20

ER -

Enantioselective protonation/diastereoselective reduction with sodium naphthalenide-acetamide; a new synthesis of chiral trans-2-phenylcyclohexanol

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