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Transition‐Metal‐Catalyzed Allylic Substitutions of Trichloroacetimidates
Author(s) -
Arnold Jeffrey S.,
Zhang Qi,
Nguyen Hien M.
Publication year - 2014
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.201402097
Subject(s) - chemistry , allylic rearrangement , enantioselective synthesis , heteroatom , nucleophile , catalysis , transition metal , nucleophilic substitution , leaving group , substitution reaction , stereochemistry , combinatorial chemistry , organic chemistry , ring (chemistry)
With the development of practical methods for their preparation, trichloroacetimidates have proven to be valuable substrates for use in carbohydrate and organic synthesis. The broad utility of allyl trichloroacetimidates for the construction of carbon‐heteroatom bonds is the result of the unique features of the trichloroacetimidate nitrogen functionality as a directing, nucleophilic, and leaving group. In this review we describe the expansion of Overman's [3,3]‐rearrangement of allyl trichloroacetimidates to allylic substitution reactions for regio‐ and enantioselective C–N, C–O, and C–F bond‐forming methodologies.