Isothiourea-Mediated Asymmetric O- to C-Carboxyl Transfer of Oxazolyl Carbonates: Structure–Selectivity Profiles and Mechanistic Studies

✍ Scribed by Caroline Joannesse; Craig P. Johnston; Louis C. Morrill; Philip A. Woods; Madeleine Kieffer; Dipl.-Chem. Tobias A. Nigst; Prof. Herbert Mayr; Dr. Tomas Lebl; Prof. Douglas Philp; Dr. Ryan A. Bragg; Dr. Andrew D. Smith

• Publisher: John Wiley and Sons
• Year: 2012
• Tongue: English
• Weight: 773 KB
• Volume: 18
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.201102847

✦ Synopsis

Abstract

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.