Asymmetric tandem reactions of N-sulfonylimines and α,β-unsaturated aldehydes: an alternative reaction pathway to that of using saturated aldehydes

被引：33

作者：

An, Qianjin ^{[1
]}

Li, Jing ^{[1
]}

Shen, Jiefeng ^{[1
]}

Butt, Nicholas ^{[1
]}

Liu, Delong ^{[1
]}

Liu, Yangang ^{[1
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 05期

基金：

中国国家自然科学基金;

关键词：

ORGANOCATALYTIC DOMINO REACTIONS; DIELS-ALDER REACTIONS; CYCLIC KETIMINES; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; TRANSFER HYDROGENATION; MICHAEL ADDITION; PIPERIDINES; ACIDS; STEREOCENTERS;

D O I：

10.1039/c4cc07051h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An organocatalyzed asymmetric tandem reaction of cyclic N-sulfonylimines and alpha,beta-unsaturated aldehydes was developed. These substrates follow an alternative reaction pathway to that of reactions involving saturated aldehydes, affording similar piperidine derivatives.

引用

页码：885 / 888

页数：4

共 50 条

[1] Direct Asymmetric Michael Addition of Cyclic N-Sulfonylimines to α,β-Unsaturated Aldehydes
Xiong, Xiao-Feng
Zhang, Hang
Peng, Jing
Chen, Ying-Chun
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) : 2358 - 2360
[2] Asymmetric Domino Reaction of Cyclic N-Sulfonylimines and Simple Aldehydes with trans-Perhydroindolic Acid as an Organocatalyst
An, Qianjin
Shen, Jiefeng
Butt, Nicholas
Liu, Delong
Liu, Yangang
Zhang, Wanbin
ORGANIC LETTERS, 2014, 16 (17) : 4496 - 4499
[3] Asymmetric transfer hydrogenation reactions of N-sulfonylimines by using alcohols as hydrogen sources
Yang, Fan
Chen, Jingchao
Shen, Guoli
Zhang, Xuexin
Fan, Baomin
CHEMICAL COMMUNICATIONS, 2018, 54 (39) : 4963 - 4966
[4] FORMATION OF MUTAGENIC UNSATURATED ALDEHYDES BY REACTIONS BETWEEN SATURATED ALDEHYDES AND AMINO-ACIDS
YAMAGUCHI, T
MUTATION RESEARCH, 1984, 130 (05): : 384 - 384
[5] Stereocontrol in Asymmetric SE′ Reactions of γ-Substituted α,β-Unsaturated Aldehydes
Williams, David R.
Atwater, Bruce A.
Bawel, Seth A.
Ke, Pucheng
Gutierrez, Osvaldo
Tantillo, Dean J.
ORGANIC LETTERS, 2014, 16 (02) : 468 - 471
[6] Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes
Galzerano, Patrizia
Pesciaioli, Fabio
Mazzanti, Andrea
Bartoli, Giuseppe
Melchiorre, Paolo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (42) : 7892 - 7894
[7] Organocatalytic Asymmetric Michael Reactions of Cyclic N-Sulfonylimines with Nitroalkenes or 2-Nitroallylic Acetates
Kim, Yurim
Kim, Yeongju
Kim, Sung-Gon
ORGANIC LETTERS, 2025, 27 (13) : 3349 - 3354
[8] Organocatalytic Asymmetric Triple Domino Reactions of Nitromethane with α,β-Unsaturated Aldehydes
Enders, Dieter
Jeanty, Matthieu
Bats, Jan W.
SYNLETT, 2009, (19) : 3175 - 3178
[9] Conversion of α,β-unsaturated aldehydes into saturated esters:: An umpolung reaction catalyzed by nucleophilic carbenes
Chan, A
Scheidt, KA
ORGANIC LETTERS, 2005, 7 (05) : 905 - 908
[10] REACTION OF Nβ-BENZYLSEROTONIN WITH α,β-UNSATURATED AND ARYL ALDEHYDES IN THE PRESENCE OF A BASE
Yamada, Koji
Namerikawa, Yuichi
Abe, Takumi
Ishikura, Minoru
HETEROCYCLES, 2009, 77 (02) : 825 - 828

← 1 2 3 4 5 →