Modular synthesis of bis-α-chiral amines using Ellman sulfinamide for consecutive S -to- C chirality induction/transfer

Science Advances, Journal Year: 2025, Volume and Issue: 11(14)

Published: April 4, 2025

Amines are ubiquitous components in pharmaceuticals. Increasing saturated substitutions ( sp 3 -hybridized carbon) at the amino center and number of chiral centers can enrich molecular diversity chemical space, ultimately enhancing success drug development. However, synthesis such advanced amines is challenging due to a higher level structural complexity stereo-control. Here, we report modular protocol for short de novo bis-α-chiral amines. This uses commercially available Ellman sulfinamide, tert -butanesulfinamide t BS), as exclusive source selectively produce all possible stereoisomers. Sequential formation contiguous α-amino carbons achieved by chirality induction transfer mechanisms that both enabled BS, stereoselective imine functionalization alkyne-participated rearrangement reaction. The second step developed crucial high diastereoselectivity, which problematic previous methods. other coupling partners used this abundant feedstocks, providing desirable products.

Language: Английский

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Enantioselective Formal 1,2-Diamination of Ketenes with Iminosulfinamides: Asymmetric Synthesis of Unnatural α,α-Disubstituted α-Amino Acid Derivatives

Organic Letters, Journal Year: 2024, Volume and Issue: 26(16), P. 3447 - 3452

Published: April 11, 2024

A method was developed for the enantioselective formal 1,2-diamination of disubstituted ketenes using iminosulfinamides as nitrogen sources. The protocol involves addition lithium to form N-iminosulfinyl amide metalloenolates. These metalloenolates then undergo a [2,3]-sigmatropic rearrangement yield unnatural α,α-disubstituted α-amino acid derivatives with high enantiopurity. chirality present at sulfur atom in is effectively transferred α carbon resulting products, facilitating highly amination ketenes.

Language: Английский

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Synthesis of Optically Active Amino Amides

Synfacts, Journal Year: 2024, Volume and Issue: 20(05), P. 0556 - 0556

Published: April 15, 2024

Key words α-amino acids - chiral sulfonamides alkynes [2,3]-Sigmatropic Rearrangement

Language: Английский

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Recent progress in the asymmetric construction of C N, C O, and C S bonds using chiral sulfinamide reagents

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 148, P. 155243 - 155243

Published: Aug. 5, 2024

Language: Английский

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