Double Axially Chiral Bisphosphorylimides Catalyzed Highly Enantioselective and Efficient Friedel-Crafts Reaction of Indoles with Imines

Cool cats: 1,1′‐Bi‐2‐naphthol and vaulted 3,3′‐biphenanthrol‐type bisphosphorylimides enabled the atom‐economical and highly enantioselective Friedel–Crafts reaction between indoles and N‐tosylimines with a low catalyst loading (see scheme). A very small amount of 4‐(dimethylamino)pyridine (DMAP) su...

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Published in:Chemistry : a European journal 2013-01, Vol.19 (2), p.474-478
Main Authors: Wu, Kun, Jiang, Yi-Jun, Fan, Yan-Sen, Sha, Di, Zhang, Suoqin
Format: Article
Language:English
Subjects:
asymmetric catalysis
bisphosphorylimides
Catalysis
Catalysts
Cats
Chemistry
enantioselectivity
Friedel-Crafts reaction
Imines
Indoles
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container_title Chemistry : a European journal
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creator Wu, Kun
Jiang, Yi-Jun
Fan, Yan-Sen
Sha, Di
Zhang, Suoqin
description Cool cats: 1,1′‐Bi‐2‐naphthol and vaulted 3,3′‐biphenanthrol‐type bisphosphorylimides enabled the atom‐economical and highly enantioselective Friedel–Crafts reaction between indoles and N‐tosylimines with a low catalyst loading (see scheme). A very small amount of 4‐(dimethylamino)pyridine (DMAP) suppressed the bisindole side product efficiently. The ortho‐substituted aldimine substrates performed excellently in this catalytic system.
doi_str_mv 10.1002/chem.201202900
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subjects asymmetric catalysis
bisphosphorylimides
Catalysis
Catalysts
Cats
Chemistry
enantioselectivity
Friedel-Crafts reaction
Imines
Indoles
title Double Axially Chiral Bisphosphorylimides Catalyzed Highly Enantioselective and Efficient Friedel-Crafts Reaction of Indoles with Imines
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