Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis

被引：85

作者：

Wei, Hanlin ^{[1
]}

Bao, Ming ^{[1
]}

Dong, Kuiyong ^{[1
]}

Qiu, Lihua ^{[1
]}

Wu, Bing ^{[1
]}

Hu, Wenhao ^{[1
,2
]}

Xu, Xinfang ^{[1
,2
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

[2] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 52期

基金：

中国国家自然科学基金;

关键词：

alkyne oxidation; carbene; cooperative catalysis; enantioselective; Mannich-type addition; OXO GOLD CARBENES; RELAY CATALYSIS; CARBENE/ALKYNE METATHESIS; PRACTICAL SYNTHESIS; CYCLOADDITION; ANALOGS; ALKYNES; ACCESS; REARRANGEMENT; CONSTRUCTION;

D O I：

10.1002/anie.201812140

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective Mannich-type reaction of 3-butynol and nitrones is described, which affords dihydrofuran-3-ones in good yields and with excellent enantioselectivities. The reaction is initiated by gold-catalyzed alkyne oxidation and modification of the resulting gold carbene species with a tethered hydroxy group to form enolate species; the reaction terminates with an enantioselective Mannich-type addition with the assistance of chiral phosphoric acid (CPA) and hydrogen bonding. This novel pattern of alkyne transformation involving chemical bond cleavage, and a fragment modification and reassembly process, provides an atom- and step-economic method, and is the first example of cooperative asymmetric catalysis in gold-catalyzed alkyne oxidations via an alpha-oxo gold carbene route.

引用

页码：17200 / 17204

页数：5

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