Pd-Catalyzed Asymmetric Allylic Substitution Cascade of But-2-ene-1,4-diyl Dimethyl Dicarbonate for the Synthesis of Chiral 2,3-Dihydrofurans

被引：23

作者：

Liu, Hao ^{[1
]}

Sun, Zhenliang ^{[2
]}

Xu, Kai ^{[1
]}

Zheng, Yan ^{[1
]}

Liu, Delong ^{[1
]}

Zhang, Wanbin ^{[1
,3
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China

[2] Southern Med Univ, Fengxian Hosp, Shanghai 201499, Peoples R China

[3] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Frontiers Sci Ctr Transformat Mol, Shanghai 200240, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 12期

基金：

中国国家自然科学基金;

关键词：

ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; DIASTEREODIVERGENT ACCESS; WILSON REARRANGEMENT; 4+1 CYCLOADDITIONS; DUAL CATALYSIS; ALKYLATION; HYDROGENATION; DERIVATIVES; ALLYLATION;

D O I：

10.1021/acs.orglett.0c01483

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein an efficient Pd-catalyzed asymmetric allylic substitution cascade of both (E)- and (Z)-but-2-ene-1,4-diyl dimethyl dicarbonates with alpha-substituted cyano ketones is described for the preparation of chiral 2,3-dihydrofurans in up to 97% yield with 98% ee. A suggested steric control process has been proposed to illustrate the differences in enantioselectivity between the reactions of (E)- and (Z)-allyl substrates. The cascade reaction could be conducted on a gram-scale, and the resulting product allows for several transformations.

引用

页码：4680 / 4685

页数：6

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