Organocatalyzed Asymmetric Tandem Intramolecular oxa-Michael Addition/Electrophilic Thiocyanation: Synthesis of Chiral α-Thiocyanato Flavanones

被引：16

作者：

Gao, Yong ^{[1
]}

Fu, Zhenda ^{[1
]}

Wu, Di ^{[1
]}

Yin, Hongquan ^{[1
]}

Chen, Fu-Xue ^{[1
]}

机构：

[1] Beijing Inst Technol, Sch Chem & Chem Engn, Liangxiang Campus,8 Liangxiang East Rd, Beijing 102488, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 01期

关键词：

enantioselectivity; oxa-Michael addition; electrophilic thiocyanation; flavanones; ACTIVATED ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE SYNTHESIS; CARBONYL-COMPOUNDS; BETA-KETOESTERS; CHROMANONES; REAGENT; TRIFLUOROMETHYLTHIOLATION; SELENOCYANATION; CYANATION; ALKALOIDS;

D O I：

10.1002/ajoc.202100649

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient bifunctional cinchona alkaloids-catalyzed asymmetric tandem intramolecular oxa-Michael addition/electrophilic thiocyanation of alkylidene beta-ketoesters with N-thiocyanatosuccinimide (NTS) was developed. A series of chiral alpha-thiocyanato flavanones containing two vicinal stereocenters including an all-carbon quaternary center were prepared in good yields with excellent diastereo- and enantioselectivities (up to 97% ee) under mild conditions, and a successful scale up preparation of our protocol was also demonstrated.

引用

页数：5

共 68 条

[1]

[Anonymous], 2008, ANGEW CHEM

[2] A novel organocatalytic tool for the iminium activation of α,β-unsaturated ketones [J].

Bartoli, Giuseppe ;

Melchiorre, Paolo .

SYNLETT, 2008, (12) :1759-1772

[3] Catalytic enantioselective synthesis of flavanones and chromanones [J].

Biddle, Margaret M. ;

Lin, Michael ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) :3830-+

[4] Recent advances in the chemistry of organic thiocyanates [J].

Castanheiro, Thomas ;

Suffert, Jean ;

Donnard, Morgan ;

Gulea, Mihaela .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) :494-505

[5] Gram-Scale Synthesis of 3-Sulfonyl Flavanones [J].

Chang, Meng-Yang ;

Tsai, Yu-Lin ;

Chang, Yu-Lun .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02) :1033-1043

[6] A C2-Symmetric Chiral Bis-Sulfoxide Ligand in a Rhodium-Catalyzed Reaction: Asymmetric 1,4-Addition of Sodium Tetraarylborates to Chromenones [J].

Chen, Jun ;

Chen, Junmin ;

Lang, Feng ;

Zhang, Xiangyang ;

Cun, Linfeng ;

Zhu, Jin ;

Deng, Jingen ;

Liao, Jian .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (13) :4552-+

[7] Facile Stereoselective Synthesis of Fluorinated Flavanone Derivatives via a One-Pot Tandem Reaction [J].

Cui, Haifeng ;

Li, Peng ;

Chai, Zhuo ;

Zheng, Changwu ;

Zhao, Gang ;

Zhu, Shizheng .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1400-1402

[8] DNA damage by fasicularin [J].

Dutta, S ;

Abe, H ;

Aoyagi, S ;

Kibayashi, C ;

Gates, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :15004-15005

[9] Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety [J].

El-Awa, Ahmad ;

Noshi, Mohammad N. ;

du Jourdin, Xavier Mollat ;

Fuchs, Philip L. .

CHEMICAL REVIEWS, 2009, 109 (06) :2315-2349

[10] Electrophilic α-thiocyanation of chiral and achiral N-acyl imides.: A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones [J].

Falck, J. R. ;

Gao, Shuanhu ;

Prasad, Ravi Naga ;

Koduru, Sreenivasulu Reddy .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (06) :1768-1771

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