Chiral nonracemic C2-symmetric biphenyls by desymmetrization of 6,6′,2,2′-tetramethoxy-1,1′-biphenyl

被引：16
|
作者：
Delogu, G
Fabbri, D
Dettori, MA
Forni, A
Casalone, G
机构：
[1] CNR, Ist Applicaz Tecn Chim Avanzate Problemi Agrobiol, I-07100 Sassari, Italy
[2] CNR, Ctr Relazioni Struttura & Reattivita Chim, I-20133 Milan, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 21期
关键词：
D O I：
10.1016/S0957-4166(00)00410-9
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Regioselective bromination of the title biphenyl 1 at the 3 and 3' positions and simultaneous desymmetrization of the biphenyl has been achieved. Metal-halide exchange at the 3,3' positions facilitated the introduction of functional groups in good yield. Regioselective reduction was obtained by using (CH3)(3)SiI, L-Selectride and HI according to the functional groups on the biphenyls. Resolution of 6,6',2,2'-tetramethoxy-3,3'-dimethyl-1,1'-biphenyl 3 was achieved by its conversion to the corresponding phosphorothioamidate diastereomers of the (S)-(-)-alpha -methylbenzylamine. The absolute configuration of (M)-(+)-3 was confirmed by X-ray analysis of the corresponding diastereomer. (C) 2000 Elsevier Science Ltd. All rights reserved.
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收藏
页码：4417 / 4427
页数：11
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