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/a de correspondencia de este trabajo

Producción científica: Artículo en revista indizada › Artículo › revisión exhaustiva

21 Citas (Scopus)

Resumen

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	Inglés
Páginas (desde-hasta)	3939-3940
Número de páginas	2
Publicación	Tetrahedron Letters
Volumen	40
N.º	20
DOI	https://doi.org/10.1016/S0040-4039(99)00615-2
Estado	Publicada - 14 may 1999
Publicado de forma externa	Sí

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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",

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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

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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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