Organocatalytic Direct Asymmetric Aldol Reactions of 3-Isothiocyanato Oxindoles to Ketones: Stereocontrolled Synthesis of Spirooxindoles Bearing Highly Congested Contiguous Tetrasubstituted Stereocenters

被引：191

作者：

Chen, Wen-Bing ^{[1
,3
]}

Wu, Zhi-Jun ^{[2
]}

Hu, Jing ^{[1
]}

Cun, Lin-Feng ^{[1
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

[3] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 09期

基金：

中国国家自然科学基金;

关键词：

CATALYTIC ENANTIOSELECTIVE SYNTHESIS; ALPHA-ISOTHIOCYANATO IMIDES; QUATERNARY STEREOCENTERS; CRUCIFEROUS PHYTOALEXIN; ENANTIOMERIC ENRICHMENT; STRESS METABOLITES; TERTIARY ALCOHOLS; ACID-DERIVATIVES; ALLENIC ESTERS; AMINO-ACIDS;

D O I：

10.1021/ol200724q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of a direct catalytic asymmetric intermolecular aldol reaction of 3-isothiocyanato oxindoles to simple ketones with bifunctional thiourea-tertiary amine as catalyst is reported. This strategy provides a promising approach for the asymmetric synthesis of a range of enantioenriched spirocyclic oxindoles bearing two highly congested contiguous tetrasubstituted carbon stereocenters. Versatile transformations of the spirocyclic oxindole products into other structurally diverse spirocyclic oxindoles have also been demonstrated.

引用

页码：2472 / 2475

页数：4

共 60 条

[1] Catalytic Enantioselective Aldol Additions to Ketones [J].

Adachi, Shinya ;

Harada, Toshiro .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (22) :3661-3671

[2] Direct catalytic asymmetric aldol reactions of aldehydes [J].

Bogevig, A ;

Kumaragurubaran, N ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2002, (06) :620-621

[3]

Carreira E. M., 2000, CATALYTIC ASYMMETRIC

[4] Highly Enantioselective Construction of Spiro[4H-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine [J].

Chen, Wen-Bing ;

Wu, Zhi-Jun ;

Pei, Qing-Lan ;

Cun, Lin-Feng ;

Zhang, Xiao-Mei ;

Yuan, Wei-Cheng .

ORGANIC LETTERS, 2010, 12 (14) :3132-3135

[5] Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (-)-donaxaridine and (R)-chimonamidine [J].

Chen, Wen-Bing ;

Du, Xi-Lin ;

Cun, Lin-Feng ;

Zhang, Xiao-Mei ;

Yuan, Wei-Cheng .

TETRAHEDRON, 2010, 66 (07) :1441-1446

[6] Efficient Synthesis of β-Hydroxy-α-Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imide with Aldehydes [J].

Chen, Xiaohong ;

Zhu, Yin ;

Qiao, Zhen ;

Xie, Mingsheng ;

Lin, Lili ;

Liu, Xiaohua ;

Feng, Xiaoming .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) :10124-10129

[7] Enantioselective catalytic formation of quaternary stereogenic centers [J].

Cozzi, Pier Giorgio ;

Hilgraf, Robert ;

Zimmermann, Nicole .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) :5969-5994

[8] Direct catalytic enantioselective mannich reactions:: Synthesis of protected anti-α,β-diamino acids [J].

Cutting, Gary A. ;

Stainforth, Nikki E. ;

John, Matthew P. ;

Kociok-Koehn, Gabriele ;

Willis, Michael C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (35) :10632-+

[9] Recent advances in aldolase-catalyzed asymmetric synthesis [J].

Dean, Stephen M. ;

Greenberg, William A. ;

Wong, Chi-Huey .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (8-9) :1308-1320

[10] Lewis base catalyzed, enantioselective aldol addition of methyl trichlorosilyl ketene acetal to ketones [J].

Denmark, SE ;

Fan, Y ;

Eastgate, MD .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5235-5248

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