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Electron‐Withdrawing, Biphenyl‐2,2′‐diol‐Based Compounds for Asymmetric Catalysis
Author(s) -
Gutierrez Elisa G.,
Moorhead Eric J.,
Smith Eva H.,
Lin Vivian,
Ackerman Laura K. G.,
Knezevic Claire E.,
Sun Victoria,
Grant Sharday,
Wenzel Anna G.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000070
Subject(s) - chemistry , biphenyl , catalysis , phosphoric acid , friedel–crafts reaction , alkylation , indole test , organic chemistry , derivative (finance) , diol , hydrogen , acid catalysis , brønsted–lowry acid–base theory , medicinal chemistry , financial economics , economics
Facile synthetic routes to a chiral chloro‐substituted biphenyl‐2,2′‐diyl hydrogen phosphate and a chiral O , O ‐biphenyl‐2,2′‐diyl phosphoramidothioate are described. The performance of these compounds as catalysts for the hydrophosphonylation of imines and the Friedel–Crafts alkylation of indole was investigated. In the latter reaction, the chloro‐substituted phosphoric acid derivative was found to rival the best Brønsted acid catalysts reported to date.