1,2-Additions on Chiral N-Sulfinylketimines: An Easy Access to Chiral α-Tertiary Amines - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2022

1,2-Additions on Chiral N-Sulfinylketimines: An Easy Access to Chiral α-Tertiary Amines

Résumé

Abstract Chiral 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 Introduction 2 1,2-Addition Reaction Methodologies 2.1 Organolithium Reagent Additions 2.2 Grignard Additions 2.3 Organozinc Reagent Additions 2.4 Organoindium Reagent Additions 2.5 Organoboron Reagent Additions 2.6 Strecker Reactions 2.7 Palladium-Catalyzed Reactions 2.8 Enols, Enolates, and Other Deprotonated Reagent Additions 2.9 Ylide Additions 2.10 Heteroatom Nucleophiles 2.11 Miscellaneous Reactions 3 Applications to the Synthesis of Biologically Active Molecules 4 Conclusions

Domaines

Chimie
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Dates et versions

hal-04413282 , version 1 (23-01-2024)

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Citer

Chukuka Achuenu, Sebastien Carret, Jean-François Poisson, Florian Berthiol. 1,2-Additions on Chiral N-Sulfinylketimines: An Easy Access to Chiral α-Tertiary Amines. Synthesis: Journal of Synthetic Organic Chemistry, 2022, 54 (10), pp.2309-2329. ⟨10.1055/s-0041-1737563⟩. ⟨hal-04413282⟩
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