107740-74-9Relevant articles and documents
A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis
Wang, Pan,Tao, Wen-Jie,Sun, Xiu-Li,Liao, Saihu,Tang, Yong
, p. 16849 - 16852 (2013)
An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.
Controlled racemization and asymmetric transformation of α-substituted carboxylic acids in the melt
Ebbers, Eelco J.,Ariaans, Gerry J. A.,Bruggink, Alle,Zwanenburg, Binne
, p. 3701 - 3718 (1999)
The racemization and asymmetric transformation of a series of α- substituted carboxylic acids, viz. mandelic acid, hydratropic acid, ibuprofen and naproxen, were studied. Several racemization methods for mandelic acid were studied and it was found that base-catalyzed racemization in aprotic polar solvents was the most efficient method. Moreover, a fast and mild base- catalyzed racemization reaction in the melt was developed. DBN turned out to be a very efficient racemizing base for the substrates studied. Combination of the base-catalyzed racemization in the melt with known resolution processes resulted in crystallization-induced asymmetric transformations. Treating racemic ibuprofen or hydratropic acid with 1.5-2.5 equivalents of enantiopure α-methylbenzylamine and a catalytic amount of DBN resulted in the isolation of enantiomerically enriched ibuprofen or hydratropic acid with ees of up to 75% and almost quantitative yields.
Chiral N,N′-dioxide-FeCl3 complex-catalyzed asymmetric intramolecular Cannizzaro reaction
Wu, Wangbin,Liu, Xiaohua,Zhang, Yuheng,Ji, Jie,Huang, Tianyu,Lin, Lili,Feng, Xiaoming
supporting information, p. 11646 - 11649 (2015/07/15)
An environmentally benign catalyst, the N,N′-dioxide-FeCl3 complex, has been developed for the asymmetric intramolecular Cannizzaro reaction. Aryl and alkyl glyoxal monohydrates were applied to obtain α-hydroxy acid esters with excellent results. Deuterium-label and control experiments shed light on the reaction mechanism.
Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex
Yamamoto, Yasunori,Shirai, Tomohiko,Miyaura, Norio
, p. 2803 - 2805 (2012/04/23)
The enantioselective synthesis of α-hydroxy esters by ruthenium-catalyzed 1,2-addition of arylboronic acids to tert-butyl glyoxylate is described. The use of RuCl2(PPh3)3 with (R,R)-Me-BIPAM gave optically active mandelic acids of up to 99% ee. Addition of a fluoride salt such as potassium fluoride (KF) or caesium fluoride (CsF) was effective for achieving high enantioselectivities. The Royal Society of Chemistry 2012.
