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通过高度非对映选择性和对映选择性锂化-共轭加成序列实现4,5,6-和3,4,5,6-取代氮杂环庚烷的不对称合成。

Asymmetric synthesis of 4,5,6- and 3,4,5,6-substituted azepanes by a highly diastereoselective and enantioselective lithiation-conjugate addition sequence.

作者信息

Lee Suk Joong, Beak Peter

机构信息

Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA.

出版信息

J Am Chem Soc. 2006 Feb 22;128(7):2178-9. doi: 10.1021/ja057592b.

DOI:10.1021/ja057592b
PMID:16478148
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2537463/
Abstract

Asymmetric syntheses of 4,5,6- and 3,4,5,6-substituted azepanes have been achieved by highly diastereoselective and enantioselective (-)-sparteine-mediated asymmetric lithiation-conjugate additions of N-Boc-N-(p-methoxyphenyl)-2,3-substituted allylamines to a beta-aryl alpha,beta-unsaturated ester followed by hydrolysis, cyclization, and reduction. Access to the enantiomeric adduct is provided by an invertive lithiation-stannylation-lithiation sequence.

摘要

通过高非对映选择性和对映选择性（-）-鹰爪豆碱介导的N-叔丁氧羰基-N-（对甲氧基苯基）-2,3-二取代烯丙胺与β-芳基α,β-不饱和酯的不对称锂化-共轭加成反应，随后进行水解、环化和还原反应，实现了4,5,6-和3,4,5,6-取代氮杂环庚烷的不对称合成。通过反向锂化-锡化-锂化序列可得到对映体加合物。

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本文引用的文献

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Asymmetric lithiation-substitution sequences of substituted allylamines.取代烯丙胺的不对称锂化-取代序列
J Org Chem. 2005 Jul 8;70(14):5376-86. doi: 10.1021/jo047752m.
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