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Platinum‐Catalyzed Regioselective Formation of β‐Alkoxy Ketones from Internal Alkynes
Author(s) -
Yang Daxin,
Huang Jianfeng,
Liu Bo
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000484
Subject(s) - regioselectivity , chemistry , aldol reaction , alkoxy group , catalysis , dimer , platinum , organic chemistry , medicinal chemistry , alkyl
Abstract A catalytic amount of Zeise's dimer and 15‐crown‐5 were combined to effectively promote the regioselective formation of β‐alkoxy ketones from 2‐(homopropargyloxy)ethanols in dimethoxyethane. The desired products were obtained in 59–98 % yields with up to 17:1 exo / endo regioselectivity. The methodology allows access to β‐hydroxy ketones as an aldol reaction alternative.