Citation: Wenze Shi, Yang Dong, Xihong Wang, Min Wang, Jian Liao. SOP-ligand enabled palladium-catalyzed enantioselective anti-Markovnikov hydrothioesterification of α-substituted styrenes[J]. Chinese Chemical Letters, ;2025, 36(11): 111023. doi: 10.1016/j.cclet.2025.111023 shu

SOP-ligand enabled palladium-catalyzed enantioselective anti-Markovnikov hydrothioesterification of α-substituted styrenes

Wenze Shi ^{a, b} ,
Yang Dong ^{a, b} ,
Xihong Wang ^{a, *,} ,
Min Wang ^a ,
Jian Liao ^{a, b, *,}

a.
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610213, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

wangxh@cib.ac.cn

jliao@cib.ac.cn

Received Date: 21 November 2024
Revised Date: 25 February 2025
Accepted Date: 2 March 2025
Available Online: 3 March 2025

Figures(5)

Chiral 3-aryl alkanoic acids and their derivatives present a class of highly valued framework in natural products and pharmaceuticals. Among multifarious synthetic strategies, asymmetric intermolecular hydrocarbonylation of α-alkyl styrenes exhibit high atom-economy and straightforwardness, nonetheless facing problems in simultaneously addressing the activity, chemoselectivity, regioselectivity and stereoselectivity of the strategy, which remain unresolved to date. Herein, we disclosed an enantioselective Pd-catalyzed exclusive anti-Markovnikov hydroesterification of α-alkyl styrenes with thiols (hydrothiocarbonylation). The catalytic system, consisting of Pd source, chiral sulfoxide phosphine ligand (SOP), p-TsOH·H₂O and LiCl, efficiently achieved the corresponding α-chiral 3-aryl alkanoic thioesters in excellent results (68 examples, up to 99% yield, generally 90%−98% ee). The chloride anion from lithium chloride (LiCl) acts as a coordinating ligand for palladium, promoting the activity while simultaneously enhancing stereochemical control. Moreover, the potential of the method was demonstrated by the late-stage functionalization of natural products, formal synthesis of biologically active molecules intermediates (RC-33, AM-6226) as well as intermediate analogue of R-106578.
- Pd-catalyzed,
- α-Alkyl styrenes,
- Asymmetric intermolecular hydrothiocarbonylation,
- Anti-Markovnikov selectivity,
- β-Chiral 3-aryl alkanoic thioesters
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