Stereoselective synthesis of -aryl--amino esters

An efficient stereoselective synthesis of β-aryl-β-amino esters via reduction of enantiomerically enriched N-(p-methoxy-α-methylbenzyl)enamines by catalytic hydrogenation followed by debenzylation is described.

[1]  R. Carlson,et al.  Formic acid reduction of enamines: scope of the reaction , 1985 .

[2]  Abdel-Magid Af,et al.  Chemical process synthesis of beta-amino acids and esters. , 1999 .

[3]  J A Mitchell,et al.  Potent, orally active GPIIb/IIIa antagonists containing a nipecotic acid subunit. Structure-activity studies leading to the discovery of RWJ-53308. , 1999, Journal of medicinal chemistry.

[4]  N. Kleiman,et al.  Sustained platelet glycoprotein IIb/IIIa blockade with oral xemilofiban in 170 patients after coronary stent deployment. , 1997, Circulation.

[5]  E. Marcantoni,et al.  Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters , 1994 .

[6]  R. E. Reddy,et al.  An Efficient Synthesis of (S)-(+)-Ethyl β-Amino-3-pyridinepropanoate Using Enantiopure Sulfinimines , 1996 .

[7]  J. Ellman,et al.  The tert-Butanesulfinyl Group: An Ideal Chiral Directing Group and Boc-Surrogate for the Asymmetric Synthesis and Applications of beta-Amino Acids. , 1999, The Journal of organic chemistry.

[8]  A. Abdel-Magid,et al.  An efficient stereoselective synthesis of methyl (S)-3-amino-3-(3-pyridyl)propanoate , 1999 .

[9]  J. Rico,et al.  A highly stereoselective Michael addition to an .alpha.,.beta.-unsaturated ester as the crucial step in the synthesis of a novel .beta.-amino acid-containing fibrinogen receptor antagonist , 1993 .

[10]  D. Cole Recent stereoselective synthetic approaches to β-amino acids , 1994 .

[11]  V J Hruby,et al.  Exploration of the conformational space of oxytocin and arginine-vasopressin using the electrostatically driven Monte Carlo and molecular dynamics methods. , 1998, Biopolymers.