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Isothiourea‐Mediated Asymmetric O ‐ to C ‐Carboxyl Transfer of Oxazolyl Carbonates: Structure–Selectivity Profiles and Mechanistic Studies
Author(s) -
Joannesse Caroline,
Johnston Craig P.,
Morrill Louis C.,
Woods Philip A.,
Kieffer Madeleine,
Nigst Tobias A.,
Mayr Herbert,
Lebl Tomas,
Philp Douglas,
Bragg Ryan A.,
Smith Andrew D.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102847
Subject(s) - selectivity , chemistry , stereochemistry , catalysis , biochemistry
The structural motif within a series of tetrahydropyrimidine‐based isothioureas necessary for generating high asymmetric induction in the asymmetric Steglich rearrangement of oxazolyl carbonates is fully explored, with crossover and dynamic 19 F NMR experiments used to develop a mechanistic understanding of this transformation.