Citation: Yan-Bo Li, Yi Li, Liang Yin. Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction[J]. Chinese Chemical Letters, ;2024, 35(7): 109294. doi: 10.1016/j.cclet.2023.109294 shu

Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction

CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Centre for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China

liangyin@sioc.ac.cn

Received Date: 8 July 2023
Revised Date: 4 November 2023
Accepted Date: 9 November 2023
Available Online: 11 November 2023

Figures(9)

A copper(Ⅰ)-catalyzed diastereodivergent addition of phosphinothioates (HP(S)ROR') to α, β-unsaturated thioamides is disclosed, which constructs vicinal P-chiral and C-chiral centers in generally high diastereo- and enantioselectivities. In this reaction, the kinetic resolution of HP(S)ROR' occurs, which affords (R)-HP(S)PhOMe in high enantioselectivity in the addition with (R, R)-Ph-BPE as the ligand. It is found through control experiment that dual "soft-soft" interaction, indicated by both ¹H and ³¹P NMR experiments, is indispensable in the present reaction. The first "soft-soft" interaction between copper(Ⅰ) catalyst and HP(S)ROR' enables facile deprotonation to generate nucleophilic [Cu]-SPROR' species. The second one between the [Cu]-SPROR' species and α, β-unsaturated thioamides facilitated the nucleophilic addition. Finally, both Michael adducts and (R)-HP(S)PhOMe are easily converted to synthetically useful compounds.
- Copper catalysis,
- Asymmetric catalysis,
- Diastereodivergent synthesis,
- P-Chirality,
- "Soft-soft" interaction
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