Synthesis of β-monosubstituted α,β-unsaturated amides with Z-selectivity using diphenylphosphonoacetamides
Synthesis of β-monosubstituted α,β-unsaturated amides with Z-selectivity using diphenylphosphonoacetamides
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DOI：
10.1002/hc.20054
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发表时间：
2004-01-01
影响因子：
0.3
通讯作者：
Ohba, Y
中科院分区：
文献类型：
--
作者：
Kojima, S;Hidaka, T;Ohba, Y
本文研究了二苯基膦酰乙酰胺[（PhO）（2）P（O）CH_2CONRR ']作为Horner-Wadsworth-Emmons试剂的应用，其中酰胺氮原子上有五种不同的取代方式（2a：R，R' = CH_2 Ph; 2b：R = CH_2 Ph，R' = H; 2c：R = Me，R' = OMe; 2d：R，R' = Ph; 2 e：R，R'=（CH_2）（4））。发现2a的反应对芳香醛具有Z-选择性，选择性高达95：5。试剂2b对苯甲醛（85：15）和3-苯基丙醛（87：13）都有合理的选择性，而试剂2c仅对后者的烷基醛（83：17）有一定的效果。与2a相比，化合物2d和2 e表现出略低的选择性。(C)2004 Wiley Periodicals，Inc.
The utility of diphenylphosphonoacetamides [(PhO)(2)P(O)CH2CONRR'] as Horner-Wadsworth-Emmons reagents was examined with five different patterns of substitution upon the amide nitrogen atom (2a: R, R' = CH2Ph; 2b: R = CH2Ph, R' = H; 2c: R = Me, R' = OMe; 2d: R, R' = Ph; 2e: R, R'= (CH2)(4)). The reaction of 2a was found to be Z-selective for aromatic aldehydes with selectivities up to 95:5. Reagent 2b led to reasonable selectivity for both benzaldehyde (85:15) and 3-phenylpropionaldehyde (87:13), while 2c was somewhat effective for only the latter alkyl aldehyde (83:17). Compounds 2d and 2e exhibited slightly lower selectivities compared with 2a. (C) 2004 Wiley Periodicals, Inc.