Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution

Keiichi Hara, Shin ya Tosaki, Vijay Gnanadesikan, Hiroyuki Morimoto, Shinji Harada, Mari Sugita, Noriyuki Yamagiwa, Shigeki Matsunaga, Masakatsu Shibasaki

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Full details of the kinetic resolution of tertiary nitroaldols derived from simple ketones are described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. Using a 2:1 mixture of La-Li3-(binaphthoxide 1a)3 complex (LLB) and La-Li3-(biphenoxide 1e)3 complex, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield. Transformations of products were also investigated.

Original languageEnglish
Pages (from-to)5030-5036
Number of pages7
JournalTetrahedron
Volume65
Issue number26
DOIs
Publication statusPublished - Jun 27 2009
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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