An ionic chiral auxiliary-induced regioselective and enantioselective Yang photocyclization reaction in the crystalline state

被引：17
|
作者：
Cheung, E [1 ]
Kang, T [1 ]
Raymond, JR [1 ]
Scheffer, JR [1 ]
Trotter, J [1 ]
机构：
[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 50期
关键词：
asymmetric induction; ketones; photochemistry; Yang photocyclization;
D O I：
10.1016/S0040-4039(99)01866-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
cis-9-Decalyl aryl ketones undergo Yang photocyclization in solution to afford an approximately 1:1 mixture of two regioisomeric racemic cyclobutanols. In contrast, irradiation in the crystalline state in the presence of various ionic chiral auxiliaries leads to a single cyclobutanol in >98% enantiomeric excess. X-Ray crystallography reveals the source of the regio-, diastereo- and enantioselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8729 / 8732
页数：4
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