Some new C2-symmetric bicyclo[2.2.1]heptadiene ligands:: synthesis and catalytic activity in rhodium(I)-catalyzed asymmetric 1,4-and 1,2-additions

被引：51

作者：

Noel, Timothy ^{[1
]}

Vandyck, Koen ^{[1
]}

Van der Eycken, Johan ^{[1
]}

机构：

[1] Univ Ghent, Dept Organ Chem, Lab Organ & Bioorgan Synthesis, B-9000 Ghent, Belgium

来源：

TETRAHEDRON | 2007年 / 63卷 / 52期

关键词：

D O I：

10.1016/j.tet.2007.10.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-2-Symmetric bicyclo[2.2.1]hepta-2,5-dienes with various substituents (R=Bn, i-Bu, c-Hex, allyl) are prepared starting from the corresponding enantiomerically pure bis-triflate (R=OTf). These chiral ligands are tested and compared in rhodium(I)-catalyzed 1,4- and 1,2-addition of phenylboronic acid to cyclic enones and aryl aldehydes, respectively. Some interesting reactivity and selectivity effects due to the introduction of sterically demanding or olefinic substituents are reported. Moreover, remarkably high catalytic activity is observed for the rhodiuin(I)-catalyzed 1,2-addition. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：12961 / 12967

页数：7

共 36 条

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