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DOI: 10.1055/s-0041-1737563
1,2-Additions on Chiral N-Sulfinylketimines: An Easy Access to Chiral α-Tertiary Amines
The financial support from Centre National de la Recherche Scientifique (CNRS) and Université Grenoble Alpes is gratefully acknowledged. C. A. thanks the Nigerian government for a Tetfund grant. The authors are thankful for financial support from the Labex ARCANE and CBH-EUR-GS (ANR-17-EURE-003).
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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 aminePublication History
Received: 28 October 2021
Accepted after revision: 05 January 2022
Article published online:
09 March 2022
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