A Modified Preparation Procedure for Carbon Nanotube-Confined Nd/Na Heterobimetallic Catalyst for anti-Selective Catalytic Asymmetric Nitroaldol Reactions

作者：Sureshkumar Devarajulu; Hashimoto Kazuki; Kumagai Naoya^*; Shibasaki Masakatsu

来源：Journal of Organic Chemistry, 2013, 78(22): 11494-11500.

DOI：10.1021/jo402042s

A recyclable asymmetric metal-based catalyst is a rare entity among the vast collection of asymmetric catalysts developed so far. Recently we found that the combination of a self-assembling metal-based asymmetric catalyst and multi-walled carbon nanotubes (MWNTs) produced a highly active and recyclable catalyst in which the catalytically active metal complex was dispersed in the MWNT network. Herein we describe an improved preparation procedure and full details of a Nd/Na heterobimetallic complex confined in MWNTs. Facilitated self-assembly of the catalyst with MWNTs avoided the sacrificial use of excess chiral ligand for the formation of the heterobimetallic complex, improving the loading ratio of the catalyst components. Eighty-five percent of the catalyst components were incorporated onto MWNTs to produce the confined catalyst, which was a highly efficient and recyclable catalyst for the anti-selective asymmetric nitroaldol reaction. The requisite precautions for the catalyst preparation to elicit reproducible catalytic performance are summarized. Superior catalytic profiles over the prototype catalyst without MWNTs were revealed in the synthesis of optically active 1,2-nitroalkanols, which are key intermediates for the synthesis of therapeutics.

• 出版日期2013-11-15