Catalytic Asymmetric Nucleophilic Addition of 3-Vinyl Indoles to Imines.

Organic letters

PubMedID: 27435050

Xue JH, Shi M, Yu F, Li XY, Ren W, Fu LN, Guo QX. Catalytic Asymmetric Nucleophilic Addition of 3-Vinyl Indoles to Imines. Org Lett. 2016;.
The 3-vinyl indole is used as a nucleophile to react with aromatic and aliphatic imines. Chiral 3-substituted indoles bearing multiple functional groups are produced with up to 99% yield, a 98:2 E/Z ratio, and 97% ee. A possible mechanism is proposed to explain the observed stereoselectivities. This strategy provides an efficient way for the preparation of novel chiral 3-substituted indoles.