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Asymmetric Formation of Allylic Amines with N‐Substituted Quaternary Stereocenters by Pd II ‐Catalyzed Aza‐Claisen Rearrangements
Author(s) -
Fischer Daniel F.,
Xin Zhuoqun,
Peters René
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200702086
Subject(s) - stereocenter , allylic rearrangement , chemistry , claisen rearrangement , medicinal chemistry , catalysis , ferrocene , imidazoline receptor , stereochemistry , enantioselective synthesis , organic chemistry , biology , electrode , electrochemistry , endocrinology
With the ferrocene imidazoline palladacycle FIP‐Cl as precatalyst, quaternary N‐substituted stereocenters can be generated in an asymmetric aza‐Claisen rearrangement. Excellent enantioselectivities are obtained even if R and R′ have a similar or identical size (see scheme: e.g. 96 % ee for CH 3 /CD 3 ).