Chiral Aryliodine-Mediated Enantioselective Organocatalytic Spirocyclization: Synthesis of Spirofurooxindoles via Cascade Oxidative C-O and C-C Bond Formation

被引：49

作者：

Cao, Yang ^{[1
]}

Zhang, Xiang ^{[1
]}

Lin, Guangyu ^{[1
]}

Zhang-Negrerie, Daisy ^{[1
]}

Du, Yunfei ^{[1
,2
]}

机构：

[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin Key Lab Modern Drug Delivery & High Effic, Tianjin 300072, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 21期

基金：

中国国家自然科学基金;

关键词：

HYDROXYLATIVE PHENOL DEAROMATIZATION; HYPERVALENT IODINE CATALYSTS; 3+2 ANNULATION; CARCINOMA-CELLS; ISATINS; SPIROOXINDOLES; REAGENTS; STRATEGY; SPIROLACTONIZATION; 3-HYDROXYOXINDOLES;

D O I：

10.1021/acs.orglett.6b02816

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective organocatalytic oxidative spirocyclization of alkyl 3-oxopentanedioate monoamide derivatives leading to the formation of diverse spirofuroox-indoles with high enantioselectivity has been realized via chiral aryliodine-mediated cascade C-O and C-C bond formations. The reaction is postulated to proceed via oxidative C-O bond formation followed by oxidative C-C bond formation, with the latter being the enantioselectivity-determining step.

引用

页码：5580 / 5583

页数：4

共 49 条

[1] Catalytic Enantioselective α-Oxysulfonylation of Ketones Mediated by Iodoarenes [J].

Altermann, Sabine M. ;

Richardson, Robert D. ;

Page, T. Keri ;

Schmidt, Ruth K. ;

Holland, Edward ;

Mohammed, Umal ;

Paradine, Shauna M. ;

French, Andrew N. ;

Richter, Christine ;

Bahar, A. Masih ;

Witulski, Bernhard ;

Wirth, Thomas .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (31) :5315-5328

[2] 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

[3] Dioxindole in Asymmetric Catalytic Synthesis: Routes to Enantioenriched 3-Substituted 3-Hydroxyoxindoles and the Preparation of Maremycin A [J].

Bergonzini, Giulia ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) :971-974

[4] Asymmetric Hydroxylative Phenol Dearomatization Promoted by Chiral Binaphthylic and Biphenylic Iodanes [J].

Bosset, Cyril ;

Coffinier, Romain ;

Peixoto, Philippe A. ;

El Assal, Mourad ;

Miqueu, Karinne ;

Sotiropoulos, Jean-Marc ;

Pouysegu, Laurent ;

Quideau, Stephane .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) :9860-9864

[5] Sartorymensin, a new indole alkaloid, and new analogues of tryptoquivaline and fiscalins produced by Neosartorya siamensis (KUFC 6349) [J].

Buttachon, Suradet ;

Chandrapatya, Angsumarn ;

Manoch, Leka ;

Silva, Artur ;

Gales, Luis ;

Bruyere, Celine ;

Kiss, Robert ;

Kijjoa, Anake .

TETRAHEDRON, 2012, 68 (15) :3253-3262

[6] Organocatalytic Asymmetric Michael/Cyclization Cascade Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with α,β-Unsaturated Acyl Phosphonates for the Construction of Spirocyclic Oxindole-γ-lactones/lactams [J].

Chen, Lin ;

Wu, Zhi-Jun ;

Zhang, Ming-Liang ;

Yue, Deng-Feng ;

Zhang, Xiao-Mei ;

Xu, Xiao-Ying ;

Yuan, Wei-Cheng .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) :12668-12675

[7] 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

[8] A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols [J].

Dohi, Toshifumi ;

Maruyama, Akinobu ;

Takenaga, Naoko ;

Senami, Kento ;

Minamitsuji, Yutaka ;

Fujioka, Hiromichi ;

Caemmerer, Simon B. ;

Kita, Yasuyuki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3787-3790

[9] Asymmetric Dearomatizing Spirolactonization of Naphthols Catalyzed by Spirobiindane-Based Chiral Hypervalent Iodine Species [J].

Dohi, Toshifumi ;

Takenaga, Naoko ;

Nakae, Tomofumi ;

Toyoda, Yosuke ;

Yamasaki, Mikio ;

Shiro, Motoo ;

Fujioka, Hiromichi ;

Maruyama, Akinobu ;

Kita, Yasuyuki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (11) :4558-4566

[10] An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones [J].

Dugal-Tessier, Julien ;

O'Bryan, Elizabeth A. ;

Schroeder, Thomas B. H. ;

Cohen, Daniel T. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (20) :4963-4967

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