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Platinum‐Catalyzed Asymmetric Ring‐opening Reaction of Oxabenzonorbornadiene with Terminal Alkynes
Author(s) -
Long Yuhua,
Jiang Han,
Zou Zhifu,
Chen Kaixuan,
Fang Yali
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400174
Subject(s) - chemistry , stereocenter , ring (chemistry) , catalysis , platinum , zinc , medicinal chemistry , optically active , stereochemistry , enantioselective synthesis , organic chemistry
A novel platinum‐catalyzed asymmetric ring‐opening reaction of oxabenzonorbornadiene with terminal alkynes is described. The reaction affords optically active cis ‐2‐alkynyl‐1,2‐dihydronaphthalen‐1‐ols in moderate yields with good enantioselectivity in the presence of catalytic amounts of Pt(COD)Cl 2 /( S )‐BINAP and an excess of zinc powder. The products were obtained exclusively with the relative cis ‐configuration of the ring substituents and the prevalent (1 R ,2 S )‐configuration of the stereocenters, as determined by single crystal X‐ray diffraction analysis.