Enantioselective synthesis of tetrahydrofuran spirooxindoles via domino oxa-Michael/Michael addition reaction using a bifunctional squaramide catalyst

被引：3

作者：

Shukla, Khyati ^{[1
]}

Khushboo ^{[1
]}

Mahto, Pratibha ^{[1
]}

Singh, Vinod K. ^{[1
]}

机构：

[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 20期

关键词：

ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; 3+2 CYCLOADDITION; TANDEM REACTION; CONSTRUCTION; ADDITION/CYCLIZATION; ALLYLSILANES; DERIVATIVES; CONVENIENT; ISATINS;

D O I：

10.1039/d2ob00633b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective approach for the synthesis of tetrahydrofuran spirooxindoles via domino oxa-Michael/Michael addition reaction of gamma-hydroxyenones to isatylidene malononitriles, using a cinchona derived bifunctional squaramide catalyst has been developed. The methodology is the first success of enantioselective oxa-Michael addition to isatylidene malononitriles. The spiro products were obtained in excellent yields with moderate to good enantio- and diastereoselectivities. Scale-up of the reaction and synthetic transformation of the spiro product into structurally complex molecules have been performed.

引用

页码：4155 / 4160

页数：6

共 47 条

[1]

[Anonymous], 2013, ANGEW CHEM, V125, P10980

[2] Asymmetric Synthesis of 1,3-Dioxolanes by Organocatalytic Formal [3+2] Cycloaddition via Hemiacetal Intermediates [J].

Asano, Keisuke ;

Matsubara, Seijiro .

ORGANIC LETTERS, 2012, 14 (06) :1620-1623

[3] Recent Multiple Transition Metal Catalysed Single-Pot Reactions [J].

Burke, Anthony J. ;

Marinho, Vanda R. ;

Furtado, Olivia M. R. .

CURRENT ORGANIC SYNTHESIS, 2010, 7 (02) :94-119

[4] Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles [J].

Cao, Zhong-Yan ;

Zhou, Feng ;

Zhou, Jian .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (06) :1443-1454

[5] Cytotoxic potential of dispirooxindolo/acenaphthoquino andrographolide derivatives against MCF-7 cell line [J].

Chakraborty, Debanjana ;

Maity, Arindam ;

Jain, Chetan K. ;

Hazra, Abhijit ;

Bharitkar, Yogesh P. ;

Jha, Tarun ;

Majumder, Hemanta K. ;

Roychoudhury, Susanta ;

Mondal, Nirup B. .

MEDCHEMCOMM, 2015, 6 (04) :702-707

[6] New Hybrid-type Squaramide-Fused Amino Alcohol Organocatalyst for Enantioselective Domino Michael Addition/Cyclization Reaction of Oxoindolines with Cyclic 1,3-Diketones [J].

Chennapuram, Madhu ;

Owolabi, Isiaka Alade ;

Seki, Chigusa ;

Okuyama, Yuko ;

Kwon, Eunsang ;

Uwai, Koji ;

Tokiwa, Michio ;

Takeshita, Mitsuhiro ;

Nakano, Hiroto .

ACS OMEGA, 2018, 3 (09) :11718-11726

[7] Discovery of XEN907, a spirooxindole blocker of NaV1.7 for the treatment of pain [J].

Chowdhury, Sultan ;

Chafeev, Mikhail ;

Liu, Shifeng ;

Sun, Jianyu ;

Raina, Vandna ;

Chui, Ray ;

Young, Wendy ;

Kwan, Rainbow ;

Fu, Jianmin ;

Cadieux, Jay A. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (12) :3676-3681

[8]

Dollings P. J., 2010, [No title captured], Patent No. [WO 2010077839, 2010077839]

[9] Synthesis and cellular profiling of diverse organosilicon small molecules [J].

Franz, Annaliese K. ;

Dreyfuss, Philip D. ;

Schreiber, Stuart L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1020-1021

[10]

Groeger H, 2015, METALS METAL COMPLEX, P325, DOI [10.1002/9783527681020.ch11, DOI 10.1002/9783527681020.CH11]

← 1 2 3 4 5 →