Organocatalytic asymmetric Michael addition between 3-subsituted oxindoles and enals catalyzed by camphor sulfonyl hydrazine

被引：10

作者：

Cheng, Wen-Fu ^{[1
]}

Chen, Ling-Yan ^{[1
]}

Xu, Fang-Fang ^{[1
]}

Lin, Wei-Yu ^{[1
]}

Ren, Xinfeng ^{[1
]}

Li, Ya ^{[1
]}

机构：

[1] Shanghai Univ Engn Sci, Coll Chem & Chem Engn, 333 Longteng Rd, Shanghai 201620, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 04期

基金：

上海市自然科学基金;

关键词：

DIELS-ALDER REACTIONS; MANNICH-TYPE REACTION; ENANTIOSELECTIVE CONSTRUCTION; QUATERNARY; STEREOCENTERS; 2-OXINDOLES; SCAFFOLD; BEARING; DESIGN; JOINS;

D O I：

10.1039/c8ob02934b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organocatalytic asymmetric Michael addition between 3-substituted oxindoles and enals catalyzed by chiral camphor sulfonyl hydrazines (CaSHs) has been developed. A wide range of 3-substituted oxindoles and enals were successfully used, giving the corresponding 3,3-disubstituted oxindoles containing vicinal stereogenic carbon centers in good yields with good to excellent enantioselectivities and moderate to good diastereoselectivities (up to 89% yield, 99% ee and 99 : 1 dr).

引用

页码：885 / 891

页数：7

共 50 条

[1] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].

Austin, JF ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173

[2] Enantioselective addition of oxindoles to aliphatic α,β-unsaturated aldehydes [J].

Bravo, Natalia ;

Mon, Ignasi ;

Companyo, Xavier ;

Alba, Andrea-Nekane ;

Moyano, Albert ;

Rios, Ramon .

TETRAHEDRON LETTERS, 2009, 50 (48) :6624-6626

[3] Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine [J].

Bui, Tommy ;

Syed, Salahuddin ;

Barbas, Carlos F., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8758-+

[4] Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles [J].

Cao, Zhong-Yan ;

Zhou, Feng ;

Zhou, Jian .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (06) :1443-1454

[5] Catalytic asymmetric synthesis of 3,3-disubstituted oxindoles: diazooxindole joins the field [J].

Cao, Zhong-Yan ;

Wang, Yu-Hui ;

Zeng, Xing-Ping ;

Zhou, Jian .

TETRAHEDRON LETTERS, 2014, 55 (16) :2571-2584

[6] The α-effect in iminium ion catalysis [J].

Cavill, JL ;

Elliott, RL ;

Evans, G ;

Jones, IL ;

Platts, JA ;

Ruda, AM ;

Tomkinson, NCO .

TETRAHEDRON, 2006, 62 (2-3) :410-421

[7] Iminium ion catalysis:: Use of the α-effect in the acceleration of the Diels-Alder reaction [J].

Cavill, JL ;

Peters, JU ;

Tomkinson, NCO .

CHEMICAL COMMUNICATIONS, 2003, (06) :728-729

[8]

Chen L.-Y., 2009, SYNTHESIS-STUTTGART, V9, P1573

[9]

Chen X, 2015, NAT COMMUN, V6, DOI [10.1038/ncomms8142, 10.1038/ncomms8346]

[10] Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies [J].

Cheng, Daojuan ;

Ishihara, Yoshihiro ;

Tan, Bin ;

Barbas, Carlos F., III .

ACS CATALYSIS, 2014, 4 (03) :743-762

← 1 2 3 4 5 →