Tetrahedron p. 6799 - 6820 (1990)
Update date:2022-08-03
Topics:
Alcaide, Benito
Rodriguez-Lopez, Julian
Monge, Angeles
Perez-Garcia, Virginia
The nucleophilic addition of lithium ester enolates 3 to 2-arylamino-2-methoxy-1-phenylethanones I (synthetic equivalents of the related phenylglyoxal anils 2) Is reported. While enolates derived from α,α-dialkyl methyl esters, 3a and 3b, give addition products by attack at either the carbonyl (kinetic products) or the imino groups through a thermally controlled process, those derived from methyl dimethoxyacetate, methyl acetate and methyl propionate, 3c, 3d, and 3e. respectively, only lead to addition products to the carbonyl group. On the basis of the Isolation of all these compounds as stable products and of some transformations and crossover experiments a reasonable mechanism Is proposed for the whole process. In all cases, addition products at the imino groups can also be obtained by the SiO2-catalyzed rearrangement of the corresponding kinetic addition compounds. The synthesis of some substituted 4-benzoyl-β-lactams 8a-g Is a particularly significant feature of this work.
View MoreShantou Baokang Pharmaceutical Co., Ltd.
Contact:+86-754-88873487
Address:5/F B Block Huangshan Bldg Huangshan Rd Shantou
Quhua Zhongxing Refrigeration Technology Co.,Ltd.
Contact:+86-5708886618
Address:318 Bulding 2, No.866 Quhua Rd.,Kecheng District
Wuxi Zuping Food Science And Technology Co.,LTD.
Contact:+86-510-87210822
Address:Guanlin town
Beijing Top Science biological technology co., LTD
Contact:+86-13439059536
Address:15-1705 jre three mile, Beijing 100000,CHINA
Beijing Mashi Fine Chemical Co.,Ltd.
Contact:+86-10-61271592
Address:Room 506, Section B, Kaichi Mansion, Industrial Development
Doi:10.1016/j.bmc.2011.05.055
(2011)Doi:10.1021/jm00107a025
(1991)Doi:10.1016/S0040-4039(00)98033-X
(1990)Doi:10.1016/S0040-4020(01)90063-8
(1990)Doi:10.1002/anie.201008212
(2011)Doi:10.1021/jo201191x
(2011)