Assembly of Diverse Spirocyclic Pyrrolidines via Transient Directing Group Enabled Ortho-C(sp2)-H Alkylation of Benzaldehydes

被引：76

作者：

Li, Feng ^{[1
]}

Zhou, Yirong ^{[1
,2
]}

Yang, Heng ^{[1
]}

Liu, Dandan ^{[1
]}

Sun, Bing ^{[1
]}

Zhang, Fang-Lin ^{[1
]}

机构：

[1] Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, Wuhan 430070, Hubei, Peoples R China

[2] Jiangxi Normal Univ, Coll Chem & Chem Engn, Key Lab Funct Small Organ Mol, Minist Educ, Nanchang 330022, Jiangxi, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 01期

基金：

中国国家自然科学基金;

关键词：

C-H ACTIVATION; ALDOSE REDUCTASE INHIBITORS; N-SULFONYL IMINES; C(SP(3))-H ARYLATION; ORTHO-ALKENYLATION; ALDEHYDES; FUNCTIONALIZATION; MALEIMIDES; ACCESS; BENZAMIDES;

D O I：

10.1021/acs.orglett.7b03502

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diversity-oriented synthesis of useful spirocyclic pyrrolidines was successfully accomplished via late-stage cascade reactions of o-succinimide-substituted benzaldehydes. A catalytic amount of aniline as a transient directing group was efficient for the ruthenium-catalyzed ortho-C(sp(2))-H alkylation of benzaldehyde with maleimide. The in situ formed imine overrided a series of other traditional directing groups with excellent site selectivities. More importantly, only 0.5 mol % of ruthenium catalyst was sufficient for a 100 mmol scale-up reaction without column chromatography purification.

引用

页码：146 / 149

页数：4

共 68 条

[1] The catalytic intermolecular orthoarylation of phenols [J].

Bedford, RB ;

Coles, SJ ;

Hursthouse, MB ;

Limmert, ME .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :112-114

[2] A deciduous directing group approach for the addition of aryl and vinyl nucleophiles to maleimides [J].

Bettadapur, Kiran R. ;

Lanke, Veeranjaneyulu ;

Prabhu, Kandikere Ramaiah .

CHEMICAL COMMUNICATIONS, 2017, 53 (46) :6251-6254

[3] Ru (II)-Catalyzed C-H Activation: Ketone-Directed Novel 1,4-Addition of Ortho C-H Bond to Maleimides [J].

Bettadapur, Kiran R. ;

Lanke, Veeranjaneyulu ;

Prabhu, Kandikere Ramaiah .

ORGANIC LETTERS, 2015, 17 (19) :4658-4661

[4] Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines [J].

Bisht, Ranjana ;

Chattopadhyay, Buddhadeb .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :84-87

[5] A planning strategy for diversity-oriented synthesis [J].

Burke, MD ;

Schreiber, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :46-58

[6] Rhodium-Catalyzed Direct Annulation of Aldehydes with Alkynes Leading to Indenones: Proceeding through in Situ Directing Group Formation and Removal [J].

Chen, Shuyou ;

Yu, Jintao ;

Jiang, Yan ;

Chen, Fan ;

Cheng, Jiang .

ORGANIC LETTERS, 2013, 15 (18) :4754-4757

[7] Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group [J].

Chen, Xiao-Yang ;

Ozturk, Seyma ;

Sorensen, Erik J. .

ORGANIC LETTERS, 2017, 19 (05) :1140-1143

[8] N-Heterocyclic carbene-catalyzed sulfa-Michael addition of enals [J].

Cong, Zi-Song ;

Li, Yang-Guo ;

Du, Guang-Fen ;

Gu, Cheng-Zhi ;

Dai, Bin ;

He, Lin .

CHEMICAL COMMUNICATIONS, 2017, 53 (98) :13129-13132

[9] Selective palladium-catalyzed arylation(s) of benzaldehyde derivatives by N-heterocarbene ligands [J].

Gürbüz, N ;

Özdemir, I ;

Çetinkaya, B .

TETRAHEDRON LETTERS, 2005, 46 (13) :2273-2277

[10] Rhodium(III)-Catalyzed C(sp3)-H Alkylation of 8-Methylquinolines with Maleimides [J].

Han, Sangil ;

Park, Jihye ;

Kim, Saegun ;

Lee, Suk Hun ;

Sharma, Satyasheel ;

Mishra, Neeraj Kumar ;

Jung, Young Hoon ;

Kim, In Su .

ORGANIC LETTERS, 2016, 18 (18) :4666-4669

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