Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes via in Situ Generated Chiral Fluoride-Catalyzed Cascade Sulfa-Michael/Aldol Reaction of 1,4-Dithiane-2,5-diol and α,β-Unsaturated Ketones

被引：42

作者：

Duan, Mengying ^{[1
]}

Liu, Yidong ^{[1
]}

Ao, Jun ^{[1
]}

Xue, Lu ^{[1
]}

Luo, Shilong ^{[1
]}

Tan, Yu ^{[1
]}

Qin, Wenling ^{[1
]}

Song, Choong Eui ^{[2
]}

Yan, Hailong ^{[1
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, IDRC, Chongqing 401331, Peoples R China

[2] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 09期

关键词：

CATION-BINDING CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; KINETIC RESOLUTION; FACILE SYNTHESIS; DERIVATIVES; STEREOCENTERS; CONSTRUCTION; ALCOHOLS; BEARING; ION;

D O I：

10.1021/acs.orglett.7b00813

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral, fluoride-catalyzed asymmetric cascade sulfaMichael/aldol condensation reaction of 1,4-dithiane-2,5-diol and a series of alpha,beta-unsaturated ketones is described to access chiral trisubstituted tetrahydrothiophene derivatives. The target products, including the spiro tetrahydrothiophene derivatives bearing a five-, six-, and seven-membered ring, were highly functionalized and showed high ee value. This established protocol realized a highly enantioselective reaction with a catalytic amount of KF and Song's chiral oligoEG via in situ generated chiral fluoride to construct useful heterocyclic skeletons with great complexity.

引用

页码：2298 / 2301

页数：4

共 42 条

[1] Synthetic Routes to Chiral Nonracemic and Racemic Dihydro- And Tetrahydrothiophenes [J].

Benetti, Simonetta ;

De Risi, Carmela ;

Pollini, Gian P. ;

Zanirato, Vinicio .

CHEMICAL REVIEWS, 2012, 112 (04) :2129-2163

[2] Asymmetric Ion-Pairing Catalysis [J].

Brak, Katrien ;

Jacobsen, Eric N. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :534-561

[3] Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions [J].

Brandau, Sven ;

Maerten, Eddy ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14986-14991

[4] Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms [J].

Bueschleb, Martin ;

Dorich, Stephane ;

Hanessian, Stephen ;

Tao, Daniel ;

Schenthal, Kyle B. ;

Overman, Larry E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (13) :4156-4186

[5] Organocatalytic Carbon-Sulfur Bond-Forming Reactions [J].

Chauhan, Pankaj ;

Mahajan, Suruchi ;

Enders, Dieter .

CHEMICAL REVIEWS, 2014, 114 (18) :8807-8864

[6] The enantioselective construction of chiral spirooxindole-based 4-thiazolidinone via asymmetric catalytic formal [3+2] annulation using a bifunctional catalyst [J].

Cheng, Ping ;

Guo, Wengang ;

Chen, Ping ;

Liu, Yan ;

Du, Xin ;

Li, Can .

CHEMICAL COMMUNICATIONS, 2016, 52 (16) :3418-3421

[7] FLUORIDE-ION AS A BASE IN ORGANIC-SYNTHESIS [J].

CLARK, JH .

CHEMICAL REVIEWS, 1980, 80 (05) :429-452

[8] CHIRAL COMPLEXES POLYMERIZE METHACRYLATE ESTERS TO GIVE HELICAL POLYMERS THAT MUTAROTATE BY UNCOILING [J].

CRAM, DJ ;

SOGAH, DY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) :8301-8302

[9] CHIRAL CROWN COMPLEXES CATALYZE MICHAEL ADDITION-REACTIONS TO GIVE ADDUCTS IN HIGH OPTICAL YIELDS [J].

CRAM, DJ ;

SOGAH, GDY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (13) :625-628

[10] Biotin: A timeless challenge for total synthesis [J].

DeClercq, PJ .

CHEMICAL REVIEWS, 1997, 97 (06) :1755-1792

← 1 2 3 4 5 →