Catalytic asymmetric synthesis of polysubstituted spirocyclopropyl oxindoles: organocatalysis versus transition metal catalysis

被引：117

作者：

Cao, Zhong-Yan ^{[1
]}

Zhou, Jian ^{[1
,2
]}

机构：

[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2015年 / 2卷 / 07期

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; REVERSE-TRANSCRIPTASE INHIBITORS; 3+2 DIPOLAR CYCLOADDITION; BAYLIS-HILLMAN ADDUCTS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE CYCLOPROPANATION; 1-(1-ALKYNYL)CYCLOPROPYL KETONES; STEREOSELECTIVE CYCLOPROPANATION; INTRAMOLECULAR CYCLOPROPANATION; EFFICIENT CONSTRUCTION;

D O I：

10.1039/c5qo00092k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Spirocyclopropyl oxindoles are widely present in natural products and bioactive molecules. In addition, they play a significant role as a type of donor-acceptor (DA) cyclopropanes in catalytic reactions. Four distinct pathways have been developed for the asymmetric synthesis of this framework, which nicely show the potential of organocatalytic and metal catalyzed asymmetric cyclopropanation in the creation of spirocyclic compounds. This minireview summarizes these complementary methods to synthesise optically active spirocyclopropyl oxindoles bearing various functional groups, discusses the difference and advantages of each method, and summarizes synthetic opportunities that still exist.

引用

页码：849 / 858

页数：10

共 165 条

[1] Asymmetric Inter- and Intramolecular Cyclopropanation Reactions Catalyzed by a Reusable Macroporous-Polymer-Supported Chiral Ruthenium(II)/Phenyloxazoline Complex [J].

Abu-Elfotoh, Abdel-Moneim ;

Phomkeona, Kesiny ;

Shibatomi, Kazutaka ;

Iwasa, Seiji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) :8439-8443

[2]

Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO

[3]

2-5

[4] Catalytic Asymmetric Cyclopropanation with Diazooxindole [J].

Awata, Atsuko ;

Arai, Takayoshi .

SYNLETT, 2013, 24 (01) :29-32

[5] Strategies for the enantioselective synthesis of spirooxindoles [J].

Ball-Jones, Nicolas R. ;

Badillo, Joseph J. ;

Franz, Annaliese K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) :5165-5181

[6] Gold(I)-Catalyzed Asymmetric Cyclopropenation of Internal Alkynes [J].

Briones, John F. ;

Davies, Huw M. L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) :11916-11919

[7] Vinyldiazolactone as a vinylcarbene precursor: Highly selective C-H insertion and cyclopropanation reactions [J].

Bykowski, Darren ;

Wu, Kou-Hui ;

Doyle, Michael P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) :16038-16039

[8] 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

[9] Highly Stereoselective Olefin Cyclopropanation of Diazooxindoles Catalyzed by a C2-Symmetric Spiroketal Bisphosphine/Au(I) Complex [J].

Cao, Zhong-Yan ;

Wang, Xiaoming ;

Tan, Chen ;

Zhao, Xiao-Li ;

Zhou, Jian ;

Ding, Kuiling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (22) :8197-8200

[10] A Highly Diastereo- and Enantioselective Hg(II)-Catalyzed Cyclopropanation of Diazooxindoles and Alkenes [J].

Cao, Zhong-Yan ;

Zhou, Feng ;

Yu, Yi-Hua ;

Zhou, Jian .

ORGANIC LETTERS, 2013, 15 (01) :42-45

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