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

Authors :
Xue JH
Shi M
Yu F
Li XY
Ren W
Fu LN
Guo QX
Source :
Organic letters [Org Lett] 2016 Aug 05; Vol. 18 (15), pp. 3874-7. Date of Electronic Publication: 2016 Jul 20.
Publication Year :
2016

Abstract

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.

Details

Language :
English
ISSN :
1523-7052
Volume :
18
Issue :
15
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
27435050
Full Text :
https://doi.org/10.1021/acs.orglett.6b01880