Abstract
AbstractChiral α-tertiary amines, a motif present in α,α-disubstituted α-amino acids, in a wide range of natural products, and many drugs and drug candidates, are important targets in organic chemistry. Among the possible strategies, 1,2-addition to chiral N-sulfinylketimines is one of the best routes to form chiral α-tertiary amines with a high level of stereoselectivity. In this review, we focus first on the addition of organometallic reagents or other nucleophiles as enols or ylides to chiral N-sulfinylketimines. Then secondly we cover a selection of applications of these additions in the synthesis of valuable biologically active compounds.1 Introduction2 1,2-Addition Reaction Methodologies2.1 Organolithium Reagent Additions2.2 Grignard Additions2.3 Organozinc Reagent Additions2.4 Organoindium Reagent Additions2.5 Organoboron Reagent Additions2.6 Strecker Reactions2.7 Palladium-Catalyzed Reactions2.8 Enols, Enolates, and Other Deprotonated Reagent Additions2.9 Ylide Additions2.10 Heteroatom Nucleophiles2.11 Miscellaneous Reactions3 Applications to the Synthesis of Biologically Active Molecules4 Conclusions
Funder
Centre National de la Recherche Scientifique
Université Grenoble Alpes
LABoratoires d’EXcellence ARCANE
Tertiary Education Trust Fund
Subject
Organic Chemistry,Catalysis
Cited by
6 articles.
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