Isosterically designed chiral catalysts: Rationale, optimization and their application in enantioselective nucleophilic addition to aldehydes

被引：8

作者：

Gao, En ^{[1
,2
]}

Li, Qiao ^{[1
,2
]}

Duan, Lili ^{[1
,2
]}

Li, Lin ^{[1
,2
]}

Li, Yue-Ming ^{[1
,2
,3
]}

机构：

[1] Nankai Univ, State Key Lab Med Chem Biol, Coll Pharm, Tianjin, Peoples R China

[2] Nankai Univ, Tianjin Key Lab Mol Drug Res, Tianjin, Peoples R China

[3] Chinese Acad Sci, Key Lab Synthet Chem Nat Subst, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2020年 / 76卷 / 47期

基金：

中国国家自然科学基金;

关键词：

Enantioselective addition; Diethylzinc; Chiral N; N; '-dioxide; Aldehyde; Chiral zinc catalyst; AZA-HENRY REACTION; ARYL TRANSFER-REACTIONS; ASYMMETRIC CATALYSIS; ORGANOZINC REAGENTS; AMINO-ACIDS; LIGANDS; BINOL; DIALKYLZINCS; ARYLATION; DIETHYLZINC;

D O I：

10.1016/j.tet.2020.131648

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Proline-based N,N'-dioxide ligands were designed on the basis of isosteric approach, and were successfully applied in enantioselective nucleophilic addition to aldehydes. In the presence of 10 mol% of chiral ligand 1b, enantioselective addition of diethylzinc to aldehydes provided the corresponding secondary alcohols in up to 90% isolated yield and up to 99% ee. Similarly, using 3e as chiral ligand, enantioselective arylation and alkynylation of aldehydes also proceeded readily, leading to the desired chiral alcohols in up to 92% isolated yield at 99% ee and 80% isolated yields and up to 84% ee, respectively. The current work would shed light on expanding the structure diversity in the design of chiral ligands and chiral catalysts. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：13

共 84 条

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