Enantioselective [4+2] Cycloaddition of Cyclic N-Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones

被引：74

作者：

Liu, Yong

Kang, Tai-Ran

Liu, Quan-Zhong

Chen, Lian-Mei

Wang, Ya-Chuan

Liu, Jie

Xie, Yong-Mei

Yang, Jin-Liang

He, Long

机构：

[1] China West Normal Univ, Coll Chem & Chem Engn, Chem Synth & Pollut Control Key Lab Sichuan Prov, 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 / 23期

关键词：

DIELS-ALDER REACTIONS; ORGANOCASCADE CATALYSIS CONSTRUCTION; ONE-POT ACCESS; ASYMMETRIC-SYNTHESIS; NUCLEOPHILIC-ADDITION; IMINES; TANDEM; ESTERS; STEREOCHEMISTRY; SULFONYLIMINES;

D O I：

10.1021/ol402977w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported.

引用

页码：6090 / 6093

页数：4

共 70 条

[1] Asymmetric Synthesis of 4-Amino-4H-Chromenes by Organocatalytic Oxa-Michael/Aza-Baylis Hillman Tandem Reactions [J].

Aleman, Jose ;

Nunez, Alberto ;

Marzo, Leyre ;

Marcos, Vanesa ;

Alvarado, Cuauhtemoc ;

Garcia Ruano, Jose Luis .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (31) :9453-9456

[2] Organocatalytic enantioselective conjugate addition to alkynones [J].

Bella, M ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5672-5673

[3] Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters [J].

Bencivenni, Giorgio ;

Wu, Li-Yuan ;

Mazzanti, Andrea ;

Giannichi, Berardino ;

Pesciaioli, Fabio ;

Song, Mao-Ping ;

Bartoli, Giuseppe ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) :7200-7203

[4]

Bertelsen S., 2009, Chem. Commun, P2178

[5] Dual Catalysis in Enantioselective Oxidopyrylium-Based [5+2] Cycloadditions [J].

Burns, Noah Z. ;

Witten, Michael R. ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) :14578-14581

[6] Phosphane-Catalyzed [4+2] Annulation of Allenoates with Ketimines: Synthesis of Sultam-Fused Tetrahydropyridines [J].

Chen, Xiang-Yu ;

Ye, Song .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (29) :5723-5728

[7] A Stable Homodinuclear Biscobalt(III)-Schiff Base Complex for Catalytic Asymmetric 1,4-Addition Reactions of β-Keto Esters to Alkynones [J].

Chen, Zhihua ;

Furutachi, Makoto ;

Kato, Yuko ;

Matsunaga, Shigeki ;

Shibasaki, Masakatsu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2218-2220

[8] Catalytic Enantioselective Formal Hetero-Diels-Alder Reactions of Enones with Isatins to Give Spirooxindole Tetrahydropyranones [J].

Cui, Hai-Lei ;

Tanaka, Fujie .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (20) :6213-6216

[9] CHIRAL INDUCTION IN THE SYNTHESIS OF 4,4-DIMETHYL-1-PHENYLPENTA-1,2-DIENE (1-PH-3-T-BU-ALLENE) CATALYZED BY CHIRAL PHOSPHINE COMPLEXES OF PALLADIUM [J].

DEGRAAF, W ;

BOERSMA, J ;

VANKOTEN, G ;

ELSEVIER, CJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 378 (01) :115-124

[10] Highly Enantioselective Aldol Reactions between Acetaldehyde and Activated Acyclic Ketones Catalyzed by Chiral Primary Amines [J].

Deng, Yu-Hua ;

Chen, Jin-Quan ;

He, Long ;

Kang, Tai-Ran ;

Liu, Quan-Zhong ;

Luo, Shi-Wei ;

Yuan, Wei-Chen .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (22) :7143-7150

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