Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution

作者：Hara Keiichi; Tosaki Shin Ya; Gnanadesikan Vijay; Morimoto Hiroyuki; Harada Shinji; Sugita Mari; Yamagiwa Noriyuki; Matsunaga Shigeki^*; Shibasaki Masakatsu

来源：Tetrahedron, 2009, 65(26): 5030-5036.

DOI：10.1016/j.tet.2009.02.031

• Asymmetric catalysis
• Bifunctional catalysis
• Kinetic resolution
• Nitroaldol
• Tertiary alcohol

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-Li-3-(binaphthoxide 1a)(3) complex (LLB) and La-Li-3-(biphenoxide 1e)(3) complex, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield. Transformations of products were also investigated.

• 出版日期2009-6-27