Suzuki arylation at positions 2 and 2′of 1,1′-binaphthyls:: stereochemical result depending on the sense of polarity of substrates

被引：16

作者：

Kasák, P ^{[1
]}

Brath, H ^{[1
]}

Dubovská, M ^{[1
]}

Jurícek, M ^{[1
]}

Putala, M ^{[1
]}

机构：

[1] Comenius Univ, Fac Nat Sci, Dept Organ Chem, Bratislava 84215, Slovakia

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 04期

关键词：

arylboronic acid; binaphthyl; cross-coupling; palladium; stereoconservative; Suzuki reaction;

D O I：

10.1016/j.tetlet.2003.11.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first preparation of enantiomerically pure 1,1'-binaphthyl-2,2'-diboronic acid (by resolution) is reported. Optimization of the cross-coupling conditions was found to be crucial to achieve good yields in Suzuki arylation in approaches from both 2,2'-diiodide or 2,2'-diboronic acid (52-56%, with model p-tolyl reagents). Stereochemical results in these reactions were dramatically different: almost complete racemization starting from the 2,2'-diiodide versus complete conservation of stereogenic information from the 2,2'-diboronic acid. This novel synthetic approach, a stereoconservative Suzuki arylation of the diboronic acid, should be a valuable method for the synthesis of a new group of 2,2'-diarylated (including functionalized) binaphthyl derivatives. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：791 / 794

页数：4

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