TY - JOUR
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
N1 - Funding Information:
This work was partially supported by Grant-in-Aid for Specially Promoted Research, Grant-in-Aid for Scientific Research (S), Grant-in-Aid for Scientific Research on Priority Areas (No. 20037010, Chemistry of Concerto Catalysis) (for S.M.) from JSPS and MEXT. H.M. and S.H. thank JSPS fellowships.
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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U2 - 10.1016/j.tet.2009.02.031
DO - 10.1016/j.tet.2009.02.031
M3 - Article
AN - SCOPUS:65749105218
VL - 65
SP - 5030
EP - 5036
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 26
ER -