Issue 4, 2024

Stereodivergent conjugate reduction of α-substituted α,β-unsaturated N-sulfinyl ketimines: flexible access to challenging acyclic β,β-disubstituted enesulfinamides

Abstract

A stereoselective 1,4-reduction protocol for α-substituted α,β-unsaturated N-tert-butanesulfinyl ketimines has been developed, providing a flexible pathway to various geometry-defined acyclic β,β-disubstituted enesulfinamides featuring two electronically and sterically similar β-substituents. The reductant-controlled stereodivergent synthesis of both (Z)- and (E)-geometric isomers of these challenging enesulfinamides is achieved using L-Selectride and InBr3/nBu3SnH, respectively. This dual reductive approach enables the selective access to either geometric isomer from the C[double bond, length as m-dash]C bond position isomers of α,β-unsaturated ketimines. The utility of this method is exemplified through the enantioselective total synthesis of (–)-daucene, showcasing its synthetic applicability.

Graphical abstract: Stereodivergent conjugate reduction of α-substituted α,β-unsaturated N-sulfinyl ketimines: flexible access to challenging acyclic β,β-disubstituted enesulfinamides

Supplementary files

Article information

Article type
Research Article
Submitted
07 Dec 2023
Accepted
04 Jan 2024
First published
05 Jan 2024

Org. Chem. Front., 2024,11, 1218-1224

Stereodivergent conjugate reduction of α-substituted α,β-unsaturated N-sulfinyl ketimines: flexible access to challenging acyclic β,β-disubstituted enesulfinamides

N. Yisimayili, T. Liu, T. Xiong and C. Lu, Org. Chem. Front., 2024, 11, 1218 DOI: 10.1039/D3QO02028B

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