酶-金属共催化实现芳香酮肟的不对称还原酰化反应

Asymmetric reductive acylation of aromatic ketoximes by enzyme-metal cocatalysis.

作者信息

Han Kiwon, Park Jaiwook, Kim Mahn-Joo

机构信息

Department of Chemistry, Pohang University of Science and Technology, San-31 Hyojadong, Pohang 790-784, Korea.

出版信息

J Org Chem. 2008 Jun 6;73(11):4302-4. doi: 10.1021/jo800270n. Epub 2008 May 3.

DOI:10.1021/jo800270n

PMID:18454550

Abstract

We have developed an efficient procedure for the asymmetric synthesis of chiral amides from ketoximes. This one-pot procedure employs two different types of catalysts, Pd nanocatalyst and lipase, for three consecutive transformations including hydrogenation, racemization, and acylation. Eight ketoximes have been efficiently transformed to the corresponding amides in good yields (83-92%) and high enantiomeric excesses (93-98%).

摘要

我们已经开发出一种从酮肟不对称合成手性酰胺的有效方法。这种一锅法使用两种不同类型的催化剂，即钯纳米催化剂和脂肪酶，进行包括氢化、外消旋化和酰化在内的三个连续转化反应。八种酮肟已被高效转化为相应的酰胺，产率良好（83 - 92%），对映体过量值高（93 - 98%）。