Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles

被引：11

作者：

Kang, Jing-Wen ^{[1
]}

Li, Xiang ^{[1
]}

Chen, Fei-Yu ^{[1
]}

Luo, Yuan ^{[1
]}

Zhang, Shu-Cang ^{[1
]}

Kang, Bin ^{[1
]}

Peng, Cheng ^{[1
]}

Tian, Xu ^{[2
,3
,4
]}

Han, Bo ^{[1
]}

机构：

[1] Chengdu Univ Tradit Chinese Med, Sch Pharm, State Key Lab Breeding Base Systemat Res Dev & Ut, Chengdu 611137, Sichuan, Peoples R China

[2] Guangzhou Med Univ, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China

[3] Guangzhou Med Univ, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Guangdong, Peoples R China

[4] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China

来源：

RSC ADVANCES | 2019年 / 9卷 / 22期

基金：

中国国家自然科学基金;

关键词：

ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; HIGHLY ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; QUATERNARY STEREOCENTERS; MEDIATED AZIRIDINATION; CYCLIZATION REACTIONS; EFFICIENT SYNTHESIS; 4+1 CYCLOADDITION; QUINONE METHIDES;

D O I：

10.1039/c9ra02192b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Protecting group-controlled annulations of tetra-substituted oxindole olefins and sulfur ylides have been achieved for the synthesis of multifunctional cyclopropane- and dihydrofuran-fused spirooxindoles. Under precise annulation regulation, a variety of cyclopropane- and dihydrofuran-fused spirooxindoles containing vicinal quaternary carbon centers were produced in up to 90% yield with up to 20:1 dr. This reaction demonstrates high regio-, chemo- and diastereoselectivity, broad functional group tolerance and gram-scale capacity.

引用

页码：12255 / 12264

页数：10

共 83 条

[1] Aggarwal V., 2004, Sci. Synth, V27, P21
[2] Highly enantioselective synthesis of glycidic amides using camphor-derived sulfonium salts. Mechanism and applications in synthesis
Aggarwal, VK
Charmant, JPH
Fuentes, D
Harvey, JN
Hynd, G
Ohara, D
Picoul, W
Robiette, R
Vasse, JL
Winn, CL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) : 2105 - 2114
[3] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis
Aggarwal, VK
Winn, CL
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 611 - 620
[4] Asymmetric sulfur ylide mediated aziridination: Application in the synthesis of the side chain of taxol
Aggarwal, VK
Vasse, JL
[J]. ORGANIC LETTERS, 2003, 5 (21) : 3987 - 3990
[5] Catalytic asymmetric epoxidation of aldehydes. Optimization, mechanism, and discovery of stereoelectronic control involving a combination of anomeric and Cieplak effects in sulfur ylide epoxidations with chiral 1,3-oxathianes
Aggarwal, VK
Ford, JG
Fonquerna, S
Adams, H
Jones, RVH
Fieldhouse, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) : 8328 - 8339
[6] [Anonymous], 2005, THIEME, pA15
[7] Badillo JJ, 2010, CURR OPIN DRUG DISC, V13, P758
[8] Strategies for the enantioselective synthesis of spirooxindoles
Ball-Jones, Nicolas R.
Badillo, Joseph J.
Franz, Annaliese K.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) : 5165 - 5181
[9] Regioselective synthesis of trisubstituted 2,3-dihydrofurans from donor-acceptor cyclopropanes or from reaction of the corey ylide with α-sulfenyl-, α-sulfinyl-, or α-sulfonylenones
Bernard, AM
Frongia, A
Piras, PP
Secci, F
Spiga, M
[J]. ORGANIC LETTERS, 2005, 7 (21) : 4565 - 4568
[10] Concerning the proposed structure of (+)-laurobtusol: Spectral discrepancies with synthetic, racemic Stereoisomers
Blanchfield, JT
Chow, S
Bernhardt, PV
Kennard, CHL
Kitching, A
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (07) : 673 - 676

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