Catalytic Enantioselective Synthesis of Key Propargylic Alcohol Intermediates of the Anti-HIV Drug Efavirenz,Organic Process Research & Development

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Catalytic Enantioselective Synthesis of Key Propargylic Alcohol Intermediates of the Anti-HIV Drug Efavirenz
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-01-09 00:00:00 , DOI: 10.1021/acs.oprd.7b00376
Yu Zheng ₁ , Lilu Zhang ₁ , Eric Meggers ₁

Affiliation

The catalytic, enantioselective synthesis of key propargylic alcohol intermediates toward the synthesis of the anti-HIV drug efavirenz is reported. Using a recently reported chiral-at-ruthenium catalyst ( J. Am. Chem. Soc. 2017, 139, 4322), catalytic enantioselective alkynylations of 1-(2,5-dichlorophenyl)-2,2,2-trifluoroethanone (99% yield, 95% ee) and 1-(5-chloro-2-nitrophenyl)-2,2,2-trifluoroethanone (97% yield, 99% ee) are achieved using catalyst loadings of merely 0.2 mol % (ca. 500 TON).

中文翻译：

抗HIV药物依非韦伦的关键炔丙基醇中间体的催化对映选择性合成

据报道，关键的炔丙醇中间体对抗HIV药物依非韦伦的合成具有催化，对映选择性。使用最近报道手性在钌催化剂（J.化学会会志。 2017，139，4322），1-（2,5-二氯苯基）-2,2,2-三氟乙酮的对映选择性催化alkynylations（99％使用仅0.2 mol％（约500 TON）的催化剂负载量即可实现收率95％ee）和1-（5-氯-2-硝基苯基）-2,2,2-三氟乙酮（97％收率99％ee））。

更新日期：2018-01-09

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