Organocatalytic enantioselective α-difluoromethylketone thiolation of β-keto esters using phthalimide-SCF₂COAr.

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-05-22 DOI:10.1039/d5ob00520e

Wenning Chang, En Wang, Junqing Liang, Xusheng Shao, Xiaoyong Xu, Wu-Lin Yang, Zhong Li

引用次数: 0

Abstract

The first asymmetric α-difluoromethylketone thiolation of diverse β-keto esters using an electrophilic phthalimide-SCF₂COAr reagent (PhthN-SCF₂COAr) was reported. In the presence of cinchona-alkaloid-based catalyst (DHQD)₂PHAL, the reaction was achieved in moderate yields with a moderate to excellent enantioselectivity (up to 93% ee) under mild reaction conditions and exhibited functional group compatibility. An ammonium hydrogen-bonded induction model was proposed to rationalize the origin of enantioselectivity.

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邻苯二胺- scf2coar有机催化β-酮酯的对映选择性α-二氟甲基酮硫代化。

采用亲电性邻苯二酰亚胺- scf2coar试剂（PhthN-SCF2COAr）首次对多种β-酮酯进行了不对称α-二氟甲基酮硫代化。在以金鸡纳生物碱为基础的催化剂（DHQD）2PHAL的存在下，在温和的反应条件下，反应收率中等，对映体选择性中至优异（ee达93%），并表现出官能团相容性。提出了一种铵氢键诱导模型，使对映体选择性的来源合理化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.

Organocatalytic enantioselective α-difluoromethylketone thiolation of β-keto esters using phthalimide-SCF2COAr.

Abstract

Organocatalytic enantioselective α-difluoromethylketone thiolation of β-keto esters using phthalimide-SCF₂COAr.