Enantiospecific synthesis of pyridinylmethyl pyrrolidinemethanols and catalytic asymmetric borane reduction of prochiral ketones

Autor:	Shao‐Feng Lue, Yong-Xin Zhang, Da-Ming Du, Xiao Chen, Wen-Ting Hua
Rok vydání:	2004
Předmět:	Diphenylmethanol Organic Chemistry General Medicine Borane Alkylation Medicinal chemistry Catalysis Pyrrolidine Reduction (complexity) Inorganic Chemistry chemistry.chemical_compound chemistry Organic chemistry Proline Physical and Theoretical Chemistry Enantiomer Carbonylation
Zdroj:	Tetrahedron: Asymmetry. 15:177-182
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2003.10.037
Popis:	Three chiral pyridinylmethyl pyrrolidinemethanol derivatives have been synthesized from N -alkylation of ( S )-α,α-diphenyl-2-pyrrolidinemethanol and N -carbonylation of l -proline methyl ester. The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral oxazaborolidine catalysts prepared in situ from chiral pyridinylmethyl pyrrolidinemethanol derivatives. The corresponding chiral secondary alcohols were obtained with good to excellent enantiomeric excesses (up to 98% ee) using ( S )-2-(diphenylmethanol)-l-(2-pyridylmethyl)pyrrolidine 1 in THF at reflux and moderate to good enantiomeric excesses using C 2 -symmetric compound 2 (up to 86% ee) in THF.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::137960ef70717cc20e6b614f4d615261 https://doi.org/10.1016/j.tetasy.2003.10.037 Zobrazit plný text záznamu Full Text from ScienceDirect