Development of C2-Symmetric Chiral Spirocyclic Phase-Transfer Catalysts: Synthesis and Application to Asymmetric Alkylation of Glycinate Schiff Base

被引：20

作者：

Xu, Changming ^{[1
]}

Qi, Yinsheng ^{[1
]}

Yang, Xinshuang ^{[1
]}

Li, Xiangfan ^{[1
]}

Li, Zhenpeng ^{[1
]}

Bai, Lei ^{[2
]}

机构：

[1] Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China

[2] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 08期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; AMMONIUM-SALT; AMINO-ACIDS; HYDROGENATION; DIPHOSPHINE; LIGANDS;

D O I：

10.1021/acs.orglett.1c00535

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

yA class of C2-symmetric chiral spirocyclic phase-transfer catalysts based on tetramethyl-1,1'-spirobiindane scaffold was synthesized from commercially available bisphenol A in 12 steps with 22-25% total yields, which features a more rigid and stable backbone and smaller dihedral angles and can be easily modified. These catalysts show high catalytic performance in the asymmetric alkylation of tert-butyl glycinate Schiff base at only 2 mol % catalyst loading, giving the target products with up to 92% yield and 98% ee.

引用

页码：2890 / 2894

页数：5

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