188241-97-6Relevant articles and documents
Enantioselective catalytic ring opening of epoxides with carboxylic acids
Jacobsen, Eric N.,Kakiuchi, Fumitoshi,Konsler, Reed G.,Larrow, Jay F.,Tokunaga, Makoto
, p. 773 - 776 (1997)
The chiral Co(salen) complex 3 is an effective catalyst for the asymmetric ring-opening of meso epoxides with benzoic acid. Enantioselectivities of 55-93% were obtained with a range of substrates.
The Activation of Carboxylic Acids via Self-Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation
Monaco, Mattia Riccardo,Fazzi, Daniele,Tsuji, Nobuya,Leutzsch, Markus,Liao, Saihu,Thiel, Walter,List, Benjamin
, p. 14740 - 14749 (2016/11/18)
The heterodimerizing self-assembly between a phosphoric acid catalyst and a carboxylic acid has recently been established as a new activation mode in Br?nsted acid catalysis. In this article, we present a comprehensive mechanistic investigation on this activation principle, which eventually led to its elucidation. Detailed studies are reported, including computational investigations on the supramolecular heterodimer, kinetic studies on the catalytic cycle, and a thorough analysis of transition states by DFT calculations for the rationalization of the catalyst structure-selectivity relationship. On the basis of these investigations, we developed a kinetic resolution of racemic epoxides, which proceeds with high selectivity (up to s = 93), giving the unreacted epoxides and the corresponding protected 1,2-diols in high enantiopurity. Moreover, this approach could be advanced to an unprecedented stereodivergent resolution of racemic α-chiral carboxylic acids, thus providing access to a variety of enantiopure nonsteroidal anti-inflammatory drugs and to α-amino acid derivatives.
Erratum: Correction to Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chirally Modified AZADOs (Organic Letters (2009) 11:8 (1829-1831) DOI: 10.1021/ol900441f)
Tomizawa, Masaki,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
supporting information, p. 4968 - 4968 (2015/04/27)
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