Asymmetric synthesis of a chiral diarsine ligand via a cycloaddition reaction between 3,4-dimethy1-1-phenylarsole and diphenylvinylarsine

作者：Yao, Weiwei; Ma, Mengtao^*; Wang, Weifan; Cheng, Jianming; Xu, Li; Pullarkat, Sumod A.; Leung, Pak-Hing

来源：Tetrahedron: Asymmetry , 2014, 25(15): 1100-1103.

DOI：10.1016/j.tetasy.2014.06.005

• TERTIARY ARSINE
• 3,4-DIMETHYL-1-PHENYLARSOLE
• RESOLUTIONS
• CATALYSTS

The organopalladium complex containing ortho-metallated (S)-[1-(dimethylamino)ethyl]naphthalene as a chiral auxiliary has been successfully employed to promote the asymmetric cycloaddition reaction between 3,4-dimethyl-1-phenylarsole and diphenylvinylarsine. In the intramolecular cycloaddition reaction, a pair of separable diastereomeric palladium complexes was obtained in the ratio of 6:1. The chiral naphthylamine auxiliary could be removed chemoselectively from the template by treatment with HCI and subsequently NaI to generate the neutral diiodo complex [(As-As)PdI2]. Treatment of the diiodo complex with KCN gave the enantiomerically pure As-As bidentate ligand in quantitative yield. In contrast to the reported similar P-P and As-P analogues, both arsenic donors in the diiodo complex could be readily eliminated to produce a structurally novel dimetallic complex.

• 出版日期2014-8-15
• 单位南京中医药大学; 南京林业大学