Patent ID: 7214813

Claim:
A method of preparing enantiomerically enriched cis-cyclic β-acylaminocarbonyl derivative represented by the formula: wherein: X is selected from the group consisting of: alkyl, aryl, substituted alkyl, substituted aryl, heteroraryl, hydrogen, hydroxy, alkoxy, aryloxy, OCR 2 OR, OSiR 3 , amino, alkylamino, arylamino, dialkylamino, diarylamino, and alkylarylamino; Y and Z are independently selected from the group consisting of: hydrogen, alkyl, aryl, substituted alkyl, substituted aryl, heteroaryl, t-BuOCO (BOC), Fmoc peptide protecting group, PhCH 2 OCO (CBZ), and COOR, with the proviso that at least one of Y and Z is selected from the group consisting of: t-BuOCO (BOC), Fmoc peptide protecting group, PhCH 2 OCO (CBZ), and COOR; A is selected from the group consisting of: alkylene, substituted alkylene, alkylene of formula (CH 2 ) n wherein n is an integer from 1–10, arylene, substituted arylene, heteroarylene, (CH 2 ) l arylene(CH 2 ) m , (CH 2 ) l NR′(CH 2 ) m , (CH 2 ) l O(CH 2 ) m , (CH 2 ) l S(CH 2 ) m ; (CH 2 ) l CO(CH 2 ) m , and (CH 2 ) l C(═CH 2 )(CH 2 ) m ; wherein R′ is selected from the group consisting of: hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, acyl, COOR, t-BuOCO (BOC), Fmoc peptide protecting group, and PhCH 2 OCO (CBZ); wherein R is selected from the group consisting of: hydrogen, alkyl, substituted alkyl, aryl, and substituted aryl; and wherein each l and m is independently 0, 1, 2 or 3; said method comprising the step of: contacting hydrogen and a cyclic β-(acylamino)acrylate derivative represented by the formula: wherein the step of contacting is carried out in the presence of a Ru(II)-chiral phosphine ligand catalyst at a temperature, pressure and for a length of time sufficient to produce the enantiomerically enriched cis-cyclic β-acylaminocarbonyl derivative, wherein X, Y, Z, A, R, R′, l, m, and n have the same meaning as before.