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Platinum‐Catalyzed Cyclization of o ‐Alkynyl(oxo)benzenes with Alkenes by 1,2‐Migration of Benzene: Synthesis of 8‐Oxabicyclo[3.2.1]octane Derivatives
Author(s) -
Shu XingZhong,
Zhao ShuChun,
Ji KeGong,
Zheng ZhaoJing,
Liu XueYuan,
Liang YongMin
Publication year - 2009
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.200800888
Subject(s) - chemistry , regioselectivity , octane , benzene , platinum , catalysis , bicyclic molecule , medicinal chemistry , organic chemistry
Abstract An interesting migration of the rigid structure of benzene was observed when propargylic esters were introduced to the cyclization chemistry of o ‐alkynyl(oxo)benzene. Various 8‐oxabicyclo[3.2.1]octane derivatives with many functional groups could be synthesized from this efficient approach catalyzed by platinum. The high stereo‐ and regioselectivity involved in this transformation was also attractive.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)