Lee Suk Joong, Beak Peter
Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA.
J Am Chem Soc. 2006 Feb 22;128(7):2178-9. doi: 10.1021/ja057592b.
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.
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。