Synthesis of an enantiopure 2-arylcyclohexanols from prochiral enol acetates by an enantioselective protonation/diastereoselective reduction sequence

Gregorio Asensio; Ana Cuenca; Nuria Rodriguez; Mercedes Medio-Simón

doi:10.1016/j.tetasy.2003.09.002

Synthesis of an enantiopure 2-arylcyclohexanols from prochiral enol acetates by an enantioselective protonation/diastereoselective reduction sequence

Gregorio Asensio, Ana Cuenca, Nuria Rodriguez, Mercedes Medio-Simón

Research output: Indexed journal article › Article › peer-review

12 Citations (Scopus)

Abstract

The enantioselective protonation with 2-sulfinyl alcohols of lithium enolates of 2-arylcyclohexanones with different substituents on the phenyl group takes place with excellent enantioselectivities (89-99%). Chiral 2-phenylcyclohexanone and 2-arylcyclohexanones carrying electron donor substituents on the aromatic ring are converted into the corresponding trans-2-arylcyclohexanols by diastereoselective reduction with sodium naphthalenide in the presence of acetamide. The stereochemical integrity of the tertiary stereocenter is fully preserved using this reduction procedure. Interestingly, the chiral proton source is not consumed in the synthesis.

Original language	English
Pages (from-to)	3851-3855
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	14
Issue number	24
DOIs	https://doi.org/10.1016/j.tetasy.2003.09.002
Publication status	Published - 12 Dec 2003
Externally published	Yes

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10.1016/j.tetasy.2003.09.002

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@article{e80a97059d5e48bbaca05a115e86b3a3,

title = "Synthesis of an enantiopure 2-arylcyclohexanols from prochiral enol acetates by an enantioselective protonation/diastereoselective reduction sequence",

abstract = "The enantioselective protonation with 2-sulfinyl alcohols of lithium enolates of 2-arylcyclohexanones with different substituents on the phenyl group takes place with excellent enantioselectivities (89-99%). Chiral 2-phenylcyclohexanone and 2-arylcyclohexanones carrying electron donor substituents on the aromatic ring are converted into the corresponding trans-2-arylcyclohexanols by diastereoselective reduction with sodium naphthalenide in the presence of acetamide. The stereochemical integrity of the tertiary stereocenter is fully preserved using this reduction procedure. Interestingly, the chiral proton source is not consumed in the synthesis.",

author = "Gregorio Asensio and Ana Cuenca and Nuria Rodriguez and Mercedes Medio-Sim{\'o}n",

note = "Funding Information: Financial support by the Spanish Direcci{\'o}n General de Investigaci{\'o}n Cient{\'ı}fica y T{\'e}cnica (BQU2000-1426) and the Generalitat Valenciana (GV CTIDIB 2002/239) is gratefully acknowledged. N.R. thanks the Spanish Ministerio de Educaci{\'o}n y Ciencia and A.C. the Generalitat Valenciana for fellowships. We gratefully acknowledge the SCSIE (Universidad de Valencia) for the access to the instrumental facilities.",

year = "2003",

month = dec,

day = "12",

doi = "10.1016/j.tetasy.2003.09.002",

language = "English",

volume = "14",

pages = "3851--3855",

journal = "Tetrahedron Asymmetry",

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T1 - Synthesis of an enantiopure 2-arylcyclohexanols from prochiral enol acetates by an enantioselective protonation/diastereoselective reduction sequence

AU - Asensio, Gregorio

AU - Cuenca, Ana

AU - Rodriguez, Nuria

AU - Medio-Simón, Mercedes

N1 - Funding Information: Financial support by the Spanish Dirección General de Investigación Cientı́fica y Técnica (BQU2000-1426) and the Generalitat Valenciana (GV CTIDIB 2002/239) is gratefully acknowledged. N.R. thanks the Spanish Ministerio de Educación y Ciencia and A.C. the Generalitat Valenciana for fellowships. We gratefully acknowledge the SCSIE (Universidad de Valencia) for the access to the instrumental facilities.

PY - 2003/12/12

Y1 - 2003/12/12

N2 - The enantioselective protonation with 2-sulfinyl alcohols of lithium enolates of 2-arylcyclohexanones with different substituents on the phenyl group takes place with excellent enantioselectivities (89-99%). Chiral 2-phenylcyclohexanone and 2-arylcyclohexanones carrying electron donor substituents on the aromatic ring are converted into the corresponding trans-2-arylcyclohexanols by diastereoselective reduction with sodium naphthalenide in the presence of acetamide. The stereochemical integrity of the tertiary stereocenter is fully preserved using this reduction procedure. Interestingly, the chiral proton source is not consumed in the synthesis.

AB - The enantioselective protonation with 2-sulfinyl alcohols of lithium enolates of 2-arylcyclohexanones with different substituents on the phenyl group takes place with excellent enantioselectivities (89-99%). Chiral 2-phenylcyclohexanone and 2-arylcyclohexanones carrying electron donor substituents on the aromatic ring are converted into the corresponding trans-2-arylcyclohexanols by diastereoselective reduction with sodium naphthalenide in the presence of acetamide. The stereochemical integrity of the tertiary stereocenter is fully preserved using this reduction procedure. Interestingly, the chiral proton source is not consumed in the synthesis.

UR - http://www.scopus.com/inward/record.url?scp=0344196906&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2003.09.002

DO - 10.1016/j.tetasy.2003.09.002

M3 - Article

AN - SCOPUS:0344196906

SN - 0957-4166

VL - 14

SP - 3851

EP - 3855

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 24

ER -

Synthesis of an enantiopure 2-arylcyclohexanols from prochiral enol acetates by an enantioselective protonation/diastereoselective reduction sequence

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