You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via1.3.2.2.1.1 Amide Synthesis
Please login to access the full content or check if you have access via
Rodríguez-Mata, M.; Gotor-Fernández, V., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 203.
The hydrolase-catalyzed acylation of racemic amines has allowed the stereoselective production of a huge number of optically active amides.[17] Ethyl acetate or alkyl methoxyacetates have been widely employed as acyl donors and/or solvents due to their low cost, ease of handling, and usefulness as organic solvents in biotransformations; the alkyl methoxyacetates are key to an efficient fast acylation as the methoxy substituent increases the carbonyl activity and, therefore, the initial acylation rate. Moreover, in contrast to the reaction with other highly activated acyl donors, such as trichloroacetic acid esters, nonenzymatic side reactions do not take place.[91]
Mee eeeeeee, eeee eeeeeeeeeeeeeeeee eeeeee β-eeeeeeeeeee eeeeeeeeeeeeeee 88 eeeeeee ee eeeeeeeeeee eeee eeee eeeeeeee ee eeeee eeeeeeeeeee eeee eee ee eeee eeeeee ee eeeee ee e Meeeeee eeeeeeeeee eeeeee M (MMMM) eeeeeeee eeeeeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeee eeeeee eeeee eeeee eeeeeee ee eee eeee eeeee eee eeeeeee (Meeeee 88).[88] Mee eeeeeeee eeeeee eee ee eeeeeeeee ee e eeeeeeeeeeeeeeeee eeeeeee ee eeeee eeeee eeeeeeeeeeeee ee ee 88%.
Meeeee 88 Meeeeeeee Meeeeee Meeeeeeeee ee β-Meee-Meeeeeeeeee Meeeeeeeeeeeeee eeee Meeee Meeeeee ee eee Meee Meeee eee Meeeeee[88]
Meeeeeeee, eee eee ee eee eeee eeeee ee eeee eeeeeeee eee eeeeeee eee eeee ee e eeeeee eeeeeeeeeeeeeeee eeeeeee eeeeee ee eeeeeeeeeee eeeeeeee eeeeeeeee. Me eeee eeee, eee eeeeeee eee ee eeeeee ee eeeee eeeeeeeee eeeeeeee eeee ee eeeeeeeeeeeeeee ee eeee-eeeee eeeeee eeeee eee eeee eee ee eeeee eeeeeeeeeee ee eee eeee eeeee.[88] Meeeeee eeeeeeeee eeeeeeee eee eeeeeeeee eee eeeeeeeeeeeeeeeeee ee eee eeeeeeeee eeeeeeee ee eee eeeeeeeeeee ee eee eeeeeeeeeeeeeee ee eeeee eeeeeeee ee eeee eeeeee (e.e., 88–88) ee eeeee ee Meeeee 88 eee eee eeeeeeeeee ee 8-eeeeeeeeeeeeeeee (88) eeee eeeeeeeee eeeeeeeeeeeeee (88) ee eeee 8-eeeeeee-M-[(M)-8-eeeeeeeeeee]eeeeeeeee [(M)-88].[88,88] Meeeeee, eeee eee eee ee ee eeeee eeeeee eeeeeeee eeeee, eeeee eeeeeeeeeeeeee ee eeeeeee ee ee eee eeeeeee eeee eeeee.[88] Mee eeeeeeeee eeeeeee eee eeee eeee-eeeee eeeee eee eee eeeeeeeeeeeee eeeeee ee eeee eeeeee eeee eeeeeee eeee eeeeeeeeee eeee eeeeeeeeeeeeeeeeee (>88% ee) eeee eeeeee ee eeeeeee ee 88 °M.[88]
Meeeee 88 Meeeeeeeee ee Meee Meeeee eeee Meeee Meeeeee Meeeee eee Meeee Mee ee eee Meeeeeeeee ee 8-Meeeeeeeeeeeeeee[88,88]
Me e eeeeeee eeeeeee, M-eeee eeeeeeeeee, eeeeeeeee M-eeeeeeee eeeeeee eeeeeeeeeeeeee eeeeee 88, eeee eeeeeeeeeeee eeeee eeeeeeeee ee eeeeeeeee eeeeee ee eee eeeeee eeeeeeee eeeeeeeee eeeeeee eeeeeeeeee ee eeeeeeeee eee eeeeeeee eeeeee,[88] eee eeeeeee eeeeeeeeeeeeeeeeee eeeeeee eeeee eeeeeeee eeee eee eeeeeeeeee ee eee eeeeee eeee ee eee eee eeeeeeeeeeee ee eee eeeeeeeeeee eeeeee ee ee e eeeeeee eee ee eeeee eeeeeeeee eeeeeeeeeeeeee. Meeeee eeee eeeee eeeeeeeeeee, e.e. eee eee ee M-eeeeeeee eeeeeeeeeeeeeee eeeeeeeeeeeeee eeeee (88, M8 = Me), eee e eeeeeeeeee eeeeeeeee ee eee eeeeeeeeeeeeeeeeee.[88] Mee eeeeeeeeeeeeeeeee ee eeeee eeeeeee, ee eeeeeeeeee eeeeeeeee, ee eeeeeeee ee eeee ee eeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeee Meeeeee Meeeeeeeee ee Meeeeee Meeeee Meeee Meeeeee Meeee Meeeeeeeeee ee Meee Meeeee eee e Meeeeeee Meeeeeeeeee[88,88]
Meeeeee eee eeee eeeeeee eee eeeeeee eeeeeeeeee ee eeeeeeeeeeeeee eeeeeee. Meee, eeeeee Meeeee MMM-888 eee eeeeeeeeeeeeee eeeeeeeeeee eee ee eeeeeeee ee eee eeeeeeeeee ee e eeee ee eeeeeeeeeee, eeeee eeeee eee ee eeeeeeeeeeeeee eeeee ee eeeeeeeee eeeeee eeee, ee eeeee ee eeeeeeeee eeeeeeeee ee eee eeeeeeeee eeeee ee e eeeeeee eeeeeeeeee, eeee ee eeeeeeeee M eeeee ee >888.[888]
Meeeeeeeeeee Meeeeeeee
(M)-8-Meeeeeeeeeeeeeee [(M)-88] eee 8-Meeeeee-M-[(M)-8-eeeeeeeeeee]eeeeeeeee [(M)-88]; Meeeeee Meeeeeeee:[88]
Meeeeee 8-eeeeeeeeeeeeeeee (eee-88; 88.8 e, 8.8 eee) eee eeeeeeeee eeeeeeeeeeeeee (88; 88.8 e, 8.88 eee) eeee eeeeeeeee ee Me8M (888 eM). Meeee eee eeeeeeee ee eeeeeeeeeee MMMM (8 e), eee eeeeeeeeee eee eeeeeee (88 eee) eeeeeeeee ee ee. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee eeeeee MMMM, eee, eeee eee eeeeeee eeeeee ee eee eeeeeeeee eeeeeeeeee (M)-88 eee >88.8% eee eeee ee eee eeeee (M)-88 eee 88%, eee eeeeeeee eee eeeeeee. Mee eeeee eeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeeee eee eeeeee eeee Me8M (88 eM). Mee eeeeeeee eeeeeeeee eeee eeeeeee eeee 8% ee MMe (88 eM), eee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeee eeee M8M (888 eM). Mee eeeeeeee eeeeeee eeeeee eeee ee-eeeeeeeee eeee Me8M (8 × 88 eM) eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eeee eee eeeeeeeee eeeeeee ee eeeee (M)-88 eee eee eeeeeeeee eeeeeeeee eeeeeeeeeeeeee (88), eee eeee eee eeeeee eee eeeeeee ee eeee-ee-eeee eeeeeeeeeeee (88 °M eeee eeeeeeeeeee/8.8 eeee). Meee eeeeeeee, eee eeeee (M)-88 eeeeeeeeee ee e eeeeeeeee eeeee; eeeee: 8.88 e (88%). Meee eeeeeee ee ee eee eeee, eee eeeeeee eeeeeeee eeee eeeeeeee eeeeeeee (eM 88) ee eeeeeeee ee 88% ee MeMM. Me8M (88 eM) eee eeeee eee eee eeeeee eeee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM) eee eee eeeeeeee eeeeeeee eeee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eee eee eeeee (M)-88 eee eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee (88 °M eeee eeeeeeeeeee/8.8 eeee) eee eeeeeeee ee e eeeeeeeee eeeeee; eeeee: 8.88 e (88%).
References
[17] | eee Meeeeeee, M.; Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
[91] | Möeee, M.; Meeeeeeeeee, M. M., MeeeMeeMeee, (8888) 8, 88. |
[92] | Meeeáeee-Meeíe, M.; Meeee, M.; Meeeeeeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 8888. |
[93] | Meeeeeee-Meeeeeeeíe, M.; Meeee-Meeeáeeee, M.; Meeee, M., Mee. M. Mee. Meee., (8888), 8888. |
[94] | Meeeáeee-Meeíe, M.; Meeee, M.; Meeeeeeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 888. |
[95] | Meeeeee, M., Meeeeeeee, (8888), 8888. |
[96] | Meeeeeeeee, M.; Meee, M.; Meee, M., MeeeMeeMeee, (8888) 8, 8888. |
[97] | Meeeee, M.; Meee, M.; Meeeeeeee, M.; Meeeeeee, M. M.; Meeeeeee, M.; Mee, M., M. Mee. Meee., (8888) 88, 8888. |
[98] | Meeeee, M.; Me Meeee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M. M.; Mee, M., Mee. Meeeee. Meee., (8888) 8, 8888. |
[99] | Meeeeee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M. M.; Mee, M., Mee. Meeee. Meeee., (8888) 888, 8888. |
[100] | Meeeee, M.; Meee, M.; Meeee, M. M.; Mee, M.; Meee, M.; Meeeee, M.; Meeeeee, M. M.; Meeeeeeeeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |