Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution

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

Research output: Contribution to journalArticle

91 Citations (Scopus)

Abstract

A kinetic resolution of tertiary nitroaldols derived from simple ketones is described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. By using a mixture of La-Li3-(1a)3 complex (LLB 2a) and La-Li3-(1b)3 (LLB* 2b) complex in a ratio of 2/1, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield.

Original languageEnglish
Pages (from-to)11776-11777
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number36
DOIs
Publication statusPublished - Sep 13 2006
Externally publishedYes

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Ketones
Recovery
Kinetics
nitroaldol

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Tosaki, S. Y., Hara, K., Gnanadesikan, V., Morimoto, H., Harada, S., Sugita, M., ... Shibasaki, M. (2006). Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution. Journal of the American Chemical Society, 128(36), 11776-11777. https://doi.org/10.1021/ja064858l

Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution. / Tosaki, Shin Ya; Hara, Keiichi; Gnanadesikan, Vijay; Morimoto, Hiroyuki; Harada, Shinji; Sugita, Mari; Yamagiwa, Noriyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu.

In: Journal of the American Chemical Society, Vol. 128, No. 36, 13.09.2006, p. 11776-11777.

Research output: Contribution to journalArticle

Tosaki, SY, Hara, K, Gnanadesikan, V, Morimoto, H, Harada, S, Sugita, M, Yamagiwa, N, Matsunaga, S & Shibasaki, M 2006, 'Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution', Journal of the American Chemical Society, vol. 128, no. 36, pp. 11776-11777. https://doi.org/10.1021/ja064858l
Tosaki, Shin Ya ; Hara, Keiichi ; Gnanadesikan, Vijay ; Morimoto, Hiroyuki ; Harada, Shinji ; Sugita, Mari ; Yamagiwa, Noriyuki ; Matsunaga, Shigeki ; Shibasaki, Masakatsu. / Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution. In: Journal of the American Chemical Society. 2006 ; Vol. 128, No. 36. pp. 11776-11777.
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AU - Sugita, Mari

AU - Yamagiwa, Noriyuki

AU - Matsunaga, Shigeki

AU - Shibasaki, Masakatsu

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