Patent ID: 6770766
Filing Date: 2004-08-03
Classification: C07B,C07D

Abstract:
A process comprising epoxidizing &agr;,&bgr;-unsaturated enones or &agr;,&bgr;-unsaturated sulfones in the presence of(1) a water-soluble base, (2) an oxidant, (3) a diastereomer- and enantiomer-enriched homo-polyamino acid as catalyst, (4) water, (5) an organic solvent which is immiscible or has only limited miscibility with water, and (6) a phase-transfer catalyst of the formula (I): (R1R2R3R4A)+Xâˆ’â€ƒâ€ƒ(I) whereA is N or P, Xâˆ’ is an inorganic or organic anion, R1 and R2 are identical or different and are alkyl, aryl, aralkyl, cycloalkyl, or heteroaryl radicals that are optionally substituted by one or more identical or different halogen radicals, and R3 and R4 are identical or different and are alkyl, aryl, aralkyl, cycloalkyl, or heteroaryl radicals that are optionally substituted by one or more identical or different halogen radicals or R3 and R4 together form a C4-C6-cycloalkyl ring with A, where(i) the total of the carbon atoms and heteroatoms present in the radicals R1, R2, R3, and R4 is at least 13, and (ii) the accessibility q of the phase-transfer catalyst is in the range 0.6 to 1.3, where q is calculated from the following formula: q=&Sum;x=14[1/(total of the carbon atoms and heteroatoms in Rx)].