钯催化前手性联烯的对映选择性双硼化反应。

Palladium-catalyzed enantioselective diboration of prochiral allenes.

作者信息

Pelz Nicholas F, Woodward Angela R, Burks Heather E, Sieber Joshua D, Morken James P

机构信息

Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina, Chapel Hill, North Carolina 27599-3290, USA.

出版信息

J Am Chem Soc. 2004 Dec 22;126(50):16328-9. doi: 10.1021/ja044167u.

DOI:10.1021/ja044167u

PMID:15600327

Abstract

Pd-catalyzed diboration of prochiral allenes occurs exclusively at the internal position and is remarkably accelerated in the presence of Lewis basic ligand structures. On the basis of preliminary observations, a chiral ligand was employed, and the enantiomeric excess of a variety of diboration products was found to be in the range of 86-92% ee. The chiral diboron reaction products should be useful in organic synthesis, and preliminary experiments suggest that they may participate in allylation reactions with a high level of chirality transfer.

摘要

钯催化前手性联烯的双硼化反应仅发生在内位，并且在路易斯碱性配体结构存在下显著加速。基于初步观察，使用了手性配体，发现各种双硼化产物的对映体过量在86 - 92% ee范围内。手性双硼反应产物在有机合成中应是有用的，初步实验表明它们可能参与具有高水平手性转移的烯丙基化反应。