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

[51] STUDIES ON STRESS METABOLITES .6. SPIROBRASSININ, A NOVEL SULFUR-CONTAINING PHYTOALEXIN FROM THE DAIKON RHAPHANUS-SATIVUS L VAR HORTENSIS (CRUCIFERAE)
TAKASUGI, M
MONDE, K
KATSUI, N
SHIRATA, A
[J]. CHEMISTRY LETTERS, 1987, (08) : 1631 - 1632
[52] Design of highly enantioselective organocatalysts based on molecular recognition
Tang, Z
Cun, LF
Cui, X
Mi, AQ
Jiang, YZ
Gong, LZ
[J]. ORGANIC LETTERS, 2006, 8 (07) : 1263 - 1266
[53] A practical synthesis of (S)-2-Cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center
Tokuda, O
Kano, T
Gao, WG
Ikemoto, T
Maruoka, K
[J]. ORGANIC LETTERS, 2005, 7 (22) : 5103 - 5105
[54] Catalytic enantioselective construction of all-carbon quaternary stereocenters
Trost, BM
Jiang, CH
[J]. SYNTHESIS-STUTTGART, 2006, (03): : 369 - 396
[55] Catalytic enantioselective aldol additions of α-isothiocyanato imides to α-ketoesters
Vecchione, Matthew K.
Li, Le
Seidel, Daniel
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (25) : 4604 - 4606
[56] Paraherquamides, brevianamides, and asperparalines: Laboratory synthesis and biosynthesis. An interim report
Williams, RM
Cox, RJ
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (02) : 127 - 139
[57] The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids
Willis, MC
Cutting, GA
Piccio, VJD
Durbin, MJ
John, MP
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) : 1543 - 1545
[58] Construction of Contiguous Tetrasubstituted Chiral Carbon Stereocenters via Direct Catalytic Asymmetric Aldol Reaction of α-Isothlocyanato Esters with Ketones
Yoshino, Tatsuhiko
Morimoto, Hiroyuki
Lu, Gang
Matsunaga, Shigeki
Shibasaki, Masakatsu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (47) : 17082 - +
[59] Catalytic enantioselective intermolecular reductive aldol reaction to ketones
Zhao, DB
Oisaki, K
Kanai, M
Shibasaki, M
[J]. TETRAHEDRON LETTERS, 2006, 47 (09) : 1403 - 1407
[60] Dramatic ligand effect in catalytic asymmetric reductive aldol reaction of allenic esters to ketones
Zhao, Dongbo
Oisaki, Kounosuke
Kanai, Motomu
Shibasaki, Masakatsu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (45) : 14440 - 14441

← 1 2 3 4 5 6 →