@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.",
keywords = "Asymmetric protonation, Acid, Resolution, Arylation, Epoxides, Ketones",
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",
issn = "0957-4166",
publisher = "Elsevier Ltd.",
number = "24",
}