One-Pot Synthesis of Optically Enriched 2-Piperidinones from Aliphatic Aldehydes and Cyanoacrylamides

被引：12

作者：

He, Ying ^{[1
]}

Kang, Tai-Ran ^{[1
,2
]}

Liu, Quan-Zhong ^{[1
]}

Chen, Lian-Mei ^{[1
]}

Tu, Yi-Lian ^{[1
]}

Liu, Ya-Jun ^{[1
]}

Chen, Tang-Bin ^{[1
]}

Wang, Zhi-Qiang ^{[1
]}

Liu, Jie ^{[2
]}

Xie, Yong-Mei ^{[2
]}

Yang, Jin-Liang ^{[2
]}

He, Long ^{[1
]}

机构：

[1] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Coll Chem & Chem Engn, Nanchong 637009, Peoples R China

[2] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 16期

基金：

中国国家自然科学基金;

关键词：

ORGANOCATALYTIC MICHAEL ADDITION; DIELS-ALDER REACTION; ASYMMETRIC ALPHA-AMINATION; DOUBLE-MANNICH REACTION; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITIONS; CASCADE CYCLIZATION; EFFICIENT ACCESS; DOMINO REACTIONS; FORMAL SYNTHESIS;

D O I：

10.1021/ol401951g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective one-pot reaction of aliphatic aldehydes and cyanoacrylamides has been developed. The one-pot reaction includes an organocatalytic Michael addition followed by an intramolecular hemiaminalization. After reduction, optically enriched 2-piperidinones with three contiguous chiral centers were obtained in up to 95% yield and 9:1 dr with 99% ee.

引用

页码：4054 / 4057

页数：4

共 87 条

[61] Recent Developments in Asymmetric Organocatalytic Domino Reactions
Pellissier, Helene
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (2-3) : 237 - 294
[62] Quaternary stereogenic carbon atoms in complex molecules by an asymmetric, organocatalytic, triple-cascade reaction
Penon, Oriol
Carlone, Armando
Mazzanti, Andrea
Locatelli, Manuela
Sambri, Letizia
Bartoli, Giuseppe
Melchiorre, Paolo
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) : 4788 - 4791
[63] Structure-Based Design of Novel Inhibitors of the MDM2-p53 Interaction
Rew, Yosup
Sun, Daqing
De Turiso, Felix Gonzalez-Lopez
Bartberger, Michael D.
Beck, Hilary P.
Canon, Jude
Chen, Ada
Chow, David
Deignan, Jeffrey
Fox, Brian M.
Gustin, Darin
Huang, Xin
Jiang, Min
Jiao, Xianyun
Jin, Lixia
Kayser, Frank
Kopecky, David J.
Li, Yihong
Lo, Mei-Chu
Long, Alexander M.
Michelsen, Klaus
Oliner, Jonathan D.
Osgood, Tao
Ragains, Mark
Saiki, Anne Y.
Schneider, Steve
Toteva, Maria
Yakowec, Peter
Yan, Xuelei
Ye, Qiuping
Yu, Dongyin
Zhao, Xiaoning
Zhou, Jing
Medina, Julio C.
Olson, Steven H.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (11) : 4936 - 4954
[64] Allylic C-H Amination for the Preparation of syn-1,3-Amino Alcohol Motifs
Rice, Grant T.
White, M. Christina
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) : 11707 - 11711
[65] Asymmetric organocatalytic synthesis of γ-nitrocarbonyl compounds through Michael and Domino reactions
Roca-Lopez, David
Sadaba, David
Delso, Ignacio
Herrera, Raquel P.
Tejero, Tomas
Merino, Pedro
[J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (21-22) : 2561 - 2601
[66] FeCl3•6H2O-Catalyzed Intermolecular-Cascade Cyclization of Acetoacetanilide: Aldehyde-Tuned Synthesis to Valuable 2-Pyridone Analogues
Sengupta, Tista
Gayen, Krishnanka S.
Pandit, Palash
Maiti, Dilip K.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (07) : 1905 - 1909
[67] Recyclable Tertiary Amine Modified Diarylprolinol Ether as Aminocatalyst for the Sequential Asymmetric Synthesis of Functionalized Cyclohexanes and Chromenes
Shen, Hao
Yang, Ke-Fang
Shi, Zi-Hui
Jiang, Jian-Xiong
Lai, Guo-Qiao
Xu, Li-Wen
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (26) : 5031 - 5038
[68] New stereoselective synthesis of 2-allyl-4-nitroalkylpiperidine-2-thiones and their transformation to annulated piperidinones
Sosnicki, JG
[J]. SYNLETT, 2003, (11) : 1673 - 1677
[69] First enantioselective organocatalytic conjugate addition of aldehydes to vinyl phosphonates
Sulzer-Mosse, Sarah
Tissot, Matthieu
Alexakis, Alexandre
[J]. ORGANIC LETTERS, 2007, 9 (19) : 3749 - 3752
[70] Convenient synthesis of substituted piperidinones from α,β-unsaturated amides:: Formal synthesis of deplancheine, tacamonine, and paroxetine
Takasu, K
Nishida, N
Tomimura, A
Ihara, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) : 3957 - 3962

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