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

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

Key words

tert-butylsulfinamide - sulfinylketimine - diastereoselective - 1,2-addition - chiral α-tertiary amine

Publication History

Received: 28 October 2021

Accepted after revision: 05 January 2022

Article published online:
09 March 2022

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