Unexpected stereorecognition in nitrilase-catalyzed hydrolysis of β-hydroxy nitriles
Biocatalytic enantioselective hydrolysis of β-hydroxy nitriles to corresponding (S)-enriched β-hydroxy carboxylic acids has been achieved for the first time by an isolated nitrilase bII6402 from Bradyrhizobium japonicum USDA110. This offers a new "green" approach to optically pure β-hydroxy nitriles and β-hydroxy carboxylic acids. The observed remote stereorecognition is surprising because this nitrilase shows no enantioselectivity for the hydrolysis of α-hydroxy nitriles such as mandelonitrile.
Kamila, Sukanta,Zhu, Dunming,Biehl, Edward R.,Hua, Ling
Rhodium to the rescue: The formal aldol products of carboxamides (CONH 2) were obtained by using a RhI(OR) (R=H, Me) catalyst under essentially neutral pH and ambient conditions. This novel aldol strategy is based on the catalytic al
P(i-PrNCH2CH2)3N as a Lewis base catalyst for the synthesis of β-hydroxynitriles using TMSAN
(Equation Presented) Proazaphosphatrane 1a was found to be an efficient catalyst for synthesis of β-hydroxynitriles via the reaction of trimethylsilylacetonitrile (TMSAN) with aldehydes under mild reaction conditions and typically low catalyst loading (ca. 2 mol %). A variety of functional groups were tolerated, and good to excellent product yields were obtained.
Wadhwa, Kuldeep,Verkade, John G.
experimental part
p. 5683 - 5686
(2009/12/06)
RhI-catalyzed aldol-type reaction of organonitriles under mild conditions
An aldol-type reaction of organonitriles with aldehydes was catalyzed by a RhI(OR) species under ambient conditions, and the reaction displayed a broad substrate scope with respect to both organonitrile and aldehyde components. The Royal Societ