212776-32-4Relevant academic research and scientific papers
Nonenzymatic enantioselective monoacetylation of prochiral 2-protectedamino-2-alkyl-1,3-propanediols utilizing a chiral sulfonamide-Zn complex catalyst
Honjo, Takashi,Nakao, Michiyasu,Sano, Shigeki,Shiro, Motoo,Yamaguchi, Kentaro,Sei, Yoshihisa,Nagao, Yoshimitsu
, p. 509 - 512 (2007/10/03)
Treatment of a chiral sulfonamide with Et2Zn gave quantitatively its Zn complex and then the structure was determined by X-ray crystallographic analysis. Reaction of prochiral W-Boc-2-amino-2-alkyl-1,3-propanediols with Ac2O in the presence of 5 mol% of chiral sulfonamide - Zn complex catalyst afforded the corresponding chiral monoacetyl products in 70-92% yields with 70-88% ee values. The proposed mechanism for the catalytic monoacetylation of a prochiral 1,3-propanediol was presented on the basis of CSI-MS analysis.
New enantiodivergent procedure for the syntheses of chiral α- substituted serines from α-alkyl-α-aminomalonates utilizing enzymatic hydrolysis
Sano, Shigeki,Hayashi, Kazuhiko,Miwa, Toshio,Ishii, Takahiro,Fujii, Michiho,Mima, Hiromi,Nagao, Yoshimitsu
, p. 5571 - 5574 (2007/10/03)
Porcine liver esterase (PLE)- or rabbit liver esterase (RLE)-catalyzed hydrolysis of the pro-S ester group of diethyl α-alkyl-α- (benzyloxycarbonylamino)malonates 2a-c afforded (R)-ethyl α-alkyl-α- (benzyloxycarbonylamino)malonates 3a-c each in excellent enantiomeric excess. Enantiodivergent reductions of these acid esters 3a-c readily furnished both the corresponding enantiomeric α-substituted serines (R)- and (S)-5a-c.
