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

doi:10.1016/j.tet.2009.02.031

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 journal › Article

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 language	English
Pages (from-to)	5030-5036
Number of pages	7
Journal	Tetrahedron
Volume	65
Issue number	26
DOIs	https://doi.org/10.1016/j.tet.2009.02.031
Publication status	Published - Jun 27 2009
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution",

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.",

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T1 - Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution

AU - Hara, Keiichi

AU - Tosaki, Shin ya

AU - Gnanadesikan, Vijay

AU - Morimoto, Hiroyuki

AU - Harada, Shinji

AU - Sugita, Mari

AU - Yamagiwa, Noriyuki

AU - Matsunaga, Shigeki

AU - Shibasaki, Masakatsu

PY - 2009/6/27

Y1 - 2009/6/27

N2 - 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.

AB - 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.

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