3.4.22.6 2,4-dichlorocyclohexan-1-one + cyclohexanone yield: 43%, 80:20 anti/syn, ee (anti): 81% 3.4.22.6 2,6-dichlorocyclohexan-1-one + cyclohexanone yield: 39%, 99:01 anti/syn, ee (anti): 58% 3.4.22.6 2-chlorocyclohexan-1-one + cyclohexanone yield: 30%, 86:14 anti/syn, ee (anti): 79% 3.4.22.6 2-nitrocyclohexan-1-one + cyclohexanone yield: 24%, 87:13 anti/syn, ee (anti): 82% 3.4.22.6 3-chlorocyclohexan-1-one + cyclohexanone yield: 32%, 65:35 anti/syn, ee (anti): 93% 3.4.22.6 3-nitrocyclohexan-1-one + cyclohexanone yield: 41%, 87:13 anti/syn, ee (anti): 86% 3.4.22.6 4-bromocyclohexan-1-one + cyclohexanone yield: 29%, 81:19 anti/syn, ee (anti): 84% 3.4.22.6 4-chlorocyclohexan-1-one + cyclohexanone yield: 47%, 69:31 anti/syn, ee (anti): 75% 3.4.22.6 4-cyanobenzaldehyde + cyclohexanone catalytic activity and stereoselectivity of chymopapainare influenced by different media. Best catalytic activity and moderate stereoselectivity in DMSO (yield: 50%, anti/syn ratio 55:45, ee(anti): 40%), best enantioselectivity in CH2Cl2 (yield: 18%, anti/syn ratio: 61:39, ee(anti): 79%) 3.4.22.6 4-cyanobenzaldehyde + cyclohexanone solvent: water/MeCN. The water content greatly affects the activity and selectivity of chymopapain for the aldol reaction. The best enantioselectivity and diastereoselectivity at the water content of 0.12 (water/MeCN, v/v), which give the product in a yield of 28% with 73:27 (anti/syn ratio) and 77% ee (for anti isomer). Best enzyme activity at the water content of 0.15, which give a yield of 32% with lower selectivity