The synthesis of homochiral ligands based on [2.2]paracyclophane

被引：27
作者：
Pelter, A
Mootoo, B
Maxwell, A
Reid, A
机构：
[1] Univ Wales Swansea, Dept Chem, Swansea SA2 8PP, W Glam, Wales
[2] Univ W Indies, Dept Chem, St Augustine, Trinidad Tobago
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 47期
关键词：
homochiral ligands; 2.2]paracyclophane; ortho-lithiation; psi-geminal substitution;
D O I：
10.1016/S0040-4039(01)01808-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new ortho-lithiation of homochiral 4-N,N-diethylamido[2.2]paracyclophane 8 is the key to the production of a wide variety of 4,5-disubstituted homochiral ligands. psi -Geminal bromination of 8 proceeds in high yields and the resulting bromide may be converted into a variety of 4,13-disubstituted ligands. The o-lithiation and psi -geminal reactions can be used sequentially to give 4,5,12-trisubstituted compounds in which two liganding groups have the same geometrical relationship as in 'Phanephos'(TM). Homochiral oxazolines with only planar chirality have been made, one of which has been shown to be an effective catalyst for the Heck reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
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收藏
页码：8391 / 8394
页数：4
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