通过不对称Birch还原烷基化合成对映体纯的双环α,α-二取代螺内酰胺。

Synthesis of enantiopure bicyclic alpha,alpha-disubstituted spirolactams via asymmetric Birch reductive alkylation.

作者信息

Guéret Stéphanie M, O'Connor Patrick D, Brimble Margaret A

机构信息

Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand.

出版信息

Org Lett. 2009 Feb 19;11(4):963-6. doi: 10.1021/ol8029017.

DOI:10.1021/ol8029017

PMID:19199764

Abstract

The synthesis of enantiopure bicyclic alpha,alpha-disubstituted spirolactams is described using a diastereoselective Birch reductive alkylation as the key step. Hydrogenation of the resultant alkylated cyclohexadienes followed by intramolecular cyclization provides access to enantiopure 8-azaspiro[5.6]dodecan-7-ones.

摘要

本文描述了对映体纯的双环α,α-二取代螺内酰胺的合成方法，该方法以非对映选择性的Birch还原烷基化反应作为关键步骤。所得烷基化环己二烯经氢化后进行分子内环化反应，可得到对映体纯的8-氮杂螺[5.6]十二烷-7-酮。