Shen Zhi-Liang, Cheong Hao-Lun, Loh Teck-Peng
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
Chemistry. 2008;14(6):1875-80. doi: 10.1002/chem.200701468.
In the presence of In or Zn/AgI/InCl(3), an efficient and practical method for the Barbier-Grignard-type alkylation reactions of simple imines by using a one-pot condensation of various aldehydes, amines (including the aliphatic and chiral version), and secondary alkyl iodides has been developed. The reaction proceeded more efficiently in water than in organic solvents. Without the use of CuI, it mainly gave the imine self-reductive coupling product, which was not the alkylated product. Good diastereoselectivities (up to 92:8 dr) were obtained when L-valine methyl ester was used as the substrate.
在铟或锌/碘化银/三氯化铟存在下，通过将各种醛、胺（包括脂肪族和手性型）与仲烷基碘进行一锅缩合反应，开发了一种用于简单亚胺的巴比耶 - 格氏型烷基化反应的高效实用方法。该反应在水中比在有机溶剂中进行得更有效。不使用碘化亚铜时，主要生成亚胺自还原偶联产物，而非烷基化产物。当使用L - 缬氨酸甲酯作为底物时，可获得良好的非对映选择性（高达92:8的dr值）。
