Linearly conjugated benzocyclohexadienone photochemistry in the solid state: ionic chiral auxiliary mediated asymmetric induction

被引:18
作者
Cheung, E [1 ]
Netherton, MR [1 ]
Scheffer, JR [1 ]
Trotter, J [1 ]
机构
[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
关键词
asymmetric induction; ketones; photochemistry; pi(a)(2)+sigma(a)(2)] rearrangement;
D O I
10.1016/S0040-4039(99)01868-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric induction in the photochemistry of a linearly conjugated benzocyclohexadienone derivative has been achieved for the first time through the use of the solid state ionic chiral auxiliary method. Enantiomeric excesses as high as 70-80% at reasonable conversions are readily attainable. Crystal structures for both reactant and product are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8737 / 8740
页数:4
相关论文
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (12) :2919-2920
[2]  
QUINKERT G, 1973, PURE APPL CHEM, V33, P285, DOI DOI 10.1351/PAC197333020285
[3]  
SCHULTZ AG, 1991, CRC HDB ORGANIC PHOT, pCH58