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Synthesis of Naphthalenyl Acetate by Platinum‐Catalyzed [1,5]‐Sigmatropic Hydrogen Shift of Propargylic Esters
Author(s) -
Shu XingZhong,
Ji KeGong,
Zhao ShuChun,
Zheng ZhaoJing,
Chen Jing,
Lu Li,
Liu XueYuan,
Liang YongMin
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801591
Subject(s) - sigmatropic reaction , stereospecificity , tandem , chemistry , hydrogen , catalysis , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , composite material
A novel platinum‐catalyzed transformation of 3‐(2‐alkyl)phenyl‐propynyl acetate into naphthalenyl acetate by tandem [1,3]‐OAc shift, [1,5]‐sigmatropic hydrogen shift, and 6‐π cyclization reactions has been reported (see scheme). The [1,5]‐sigmatropic hydrogen shift of propargylic esters is described, as well as the mechanism and the stereospecificity of this tandem process.