Catalytic Asymmetric Synthesis of Isoxazolines from Silyl Nitronates

被引：33

作者：

Han, Xiaoyu ^{[1
]}

Dong, Li ^{[1
]}

Geng, Caiwei ^{[1
]}

Jiao, Peng ^{[1
]}

机构：

[1] Beijing Normal Univ, Coll Chem, Key Lab Radiopharmaceut, Beijing 100875, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 13期

基金：

中国国家自然科学基金;

关键词：

NITRILE OXIDE CYCLOADDITIONS; DIELS-ALDER REACTIONS; BETA-AMINO ACIDS; 1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; TERTIARY ENAMIDES; ENANTIOSELECTIVE SYNTHESIS; INTRAMOLECULAR ADDITION; ORGANIC-SYNTHESIS; DERIVATIVES;

D O I：

10.1021/acs.orglett.5b00826

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar Cycloadditions of triisopropylsilyl intronates and 2-alkylacroleins produced isoxazolines bearing a chiral quaternary center in high yields-and enantioselectivities with the aid of a chiral oxazaborolidine catalyst. One chiral isoxazoline product was converted to (R)-(+)-Tanikolide in 9 steps in a total yield of 43%.

引用

页码：3194 / 3197

页数：4

共 50 条

[11] Recent Advances in the Synthesis and Chemistry of Nitronates
Tabolin, Andrey A.
Sukhorukov, Alexey Yu.
Ioffe, Sema L.
Dilman, Alexander D.
SYNTHESIS-STUTTGART, 2017, 49 (15): : 3255 - 3268
[12] Catalytic Asymmetric Synthesis of Piperidines from Pyrrolidine: Concise Synthesis of L-733,060
Bilke, Julia L.
Moore, Stephen P.
O'Brien, Peter
Gilday, John
ORGANIC LETTERS, 2009, 11 (09) : 1935 - 1938
[13] Diphenylprolinol silyl ether as a catalyst in an asymmetric, catalytic and direct α-benzoyloxylation of aldehydes
Gotoh, Hiroaki
Hayashi, Yujiro
CHEMICAL COMMUNICATIONS, 2009, (21) : 3083 - 3085
[14] α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis
Zhang, Chenlong
Hu, Weipeng
Morken, James P.
ACS CATALYSIS, 2021, 11 (16) : 10660 - 10680
[15] Asymmetric Synthesis of α-Arylcyclohexenones Catalyzed by Diphenylprolinol Silyl Ether
Mehta, Ronak
Kumar, Rohtash
Singh, Suraj
Appayee, Chandrakumar
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (15) : 10892 - 10902
[16] Catalytic Asymmetric Synthesis of Isoindolinones
Gao, Wei
Chen, Mu-wang
Ding, Qiuping
Peng, Yiyuan
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (09) : 1306 - 1322
[17] Carbohydrate-based spiro bis(isoxazolines): synthesis and evaluation in asymmetric catalysis
Goyard, David
Telligmann, Susanne M.
Goux-Henry, Catherine
Boysen, Mike M. K.
Framery, Eric
Gueyrard, David
Vidal, Sebastien
TETRAHEDRON LETTERS, 2010, 51 (02) : 374 - 377
[18] Catalytic Asymmetric Synthesis of Atropisomers Featuring an Aza Axis
Feng, Jia
Lu, Chuan-Jun
Liu, Ren-Rong
ACCOUNTS OF CHEMICAL RESEARCH, 2023, 56 (18) : 2537 - 2554
[19] Recent developments in the catalytic asymmetric synthesis of α- and β-amino acids
Ma, JA
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) : 4290 - 4299
[20] Catalytic Asymmetric Synthesis of Spiropyrazolones and their Application in Medicinal Chemistry
Xie, Xin
Xiang, Li
Peng, Cheng
Han, Bo
CHEMICAL RECORD, 2019, 19 (11) : 2209 - 2235

← 1 2 3 4 5 →