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

页码：8729 / 8732

页数：4

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