Stereocontrolled construction of the dihydrothiopyrano[2,3-b]indole skeleton via an organocatalyzed asymmetric cascade sulfa-Michael-aldol reaction

被引：12

作者：

Wu, Lulu ^{[1
]}

Wang, Youming ^{[1
]}

Zhou, Zhenghong ^{[1
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Inst & State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 20-21期

基金：

中国国家自然科学基金;

关键词：

FRIEDEL-CRAFTS ALKYLATION; THIOPYRANO INDOLE-DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SIMPLE OXINDOLE; ACCESS; TETRAHYDROTHIOPHENES;

D O I：

10.1016/j.tetasy.2014.09.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We have developed an organocatalyzed asymmetric cascade sulfa-Michael-aldol reaction between 2-mercaptoindole-3-carbaldehydes and enals, which provides efficient access to the stereocontrolled construction of dihydrothiopyrano[2,3-b]indole skeletons. Under the catalysis of chiral diphenylprolinol TMS ether, the reactions ran smoothly to give the corresponding synthetically useful and pharmaceutically valuable dihydrothiopyrano[2,3-b]indoles in high yields and with 64-96% ee. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1389 / 1395

页数：7

共 43 条

[31] Access to Tetrahydrothiopyrano[2,3-b]Indole Derivatives via Zinc-Catalyzed Asymmetric [3+3] Annulation of Indoline-2-Thiones with Yne-Enones
Cui, Dan-Dan
Shi, Jian-Wen
Wang, Tong
Hua, Yuan-Zhao
Wang, Min-Can
Mei, Guang-Jian
Niu, Jun-Long
Jia, Shi-Kun
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (08) : 1770 - 1775
[32] Facile one-pot, three-component synthesis of novel bis(heterocycles) incorporating thieno[2,3-b]thiophenes via Michael addition reaction
Eid, Elshimaa M.
Hassaneen, Huwaida M. E.
Abdelhamid, Ismail A.
Elwahy, Ahmed H. M.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (05) : 2243 - 2255
[33] Synthesis of Tetrahydrothiopyrano[2,3-b]indole [60] Fullerene Derivatives via Hetero-Diels-Alder Reaction of C60 and α, β-Unsaturated Indole-2-thiones (vol 57, pg 911, 2017)
Moghaddam, Firouz Matloubi
Ghanbari, Bahram
Behzadi, Masoumeh
Baghersad, Mohammad Hadi
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (03) : 2090 - 2090
[34] Enantio- and diastereoselective synthesis of tetrahydrofuro[2,3-b]furan-2(3H)-one derivatives and related oxygen heterocycles via an asymmetric organocatalytic cascade process
Zhao, Wei-Wei
Liu, Yan-Kai
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12): : 2358 - 2363
[35] Unprecedented stereospecific synthesis of a novel tetracyclic ring system, a hybrid of tetrahydropyrrolo[2,3-b]indole and tetrahydroimidazo[1,2-a]indole, via a Domino reaction upon a tryptophan-derived amino nitrile
González-Vera, JA
García-López, MT
Herranz, R
ORGANIC LETTERS, 2004, 6 (16) : 2641 - 2644
[36] First construction of 12H-thiochromeno[2,3-b]quinolines and 5H-benzo[7,8] thiocino-[2,3-b]quinolines via intramolecular Friedel-Crafts reaction of Morita-Baylis-Hillman adducts
Zhong, Weihui
Ma, Wang
Liu, Yanbin
TETRAHEDRON, 2011, 67 (19) : 3509 - 3518
[37] CuX Dual Catalysis: Construction of Oxazolo[2,3-b][1,3]oxazines via a Tandem CuAAC/Ring Cleavage/[4+2+3] Annulation Reaction
Luo, Xiai
Yang, Zhongtao
Zheng, Jia
Liang, Gang
Luo, Hui
Yang, Weiguang
ORGANIC LETTERS, 2022, 24 (40) : 7300 - 7304
[38] Regio- and diastereoselective synthesis of new functionalized indolo[2,3-b]indole-pyrimidine based on C-N bond formation via a four-component reaction
Nasri, Shima
Rahimi, Fatemeh
Karimi, Maryam
Bayat, Mohammad
TETRAHEDRON LETTERS, 2018, 59 (23) : 2272 - 2276
[39] Rapid access of 2,3,4-trisubstituted-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole derivatives via one-pot three component reaction using organocatalysis
Singh, Shivendra
Srivastava, Anvita
Samanta, Sampak
TETRAHEDRON LETTERS, 2012, 53 (45) : 6087 - 6090
[40] 2,3,4,9-TETRAHYDROTHIOPYRANO[2,3-B]INDOLES - SYNTHESIS VIA AN INTRAMOLECULAR INDOLE GRIGNARD REACTION AND CONFORMATIONAL STUDY BY H-1 AND C-13 NMR-SPECTROSCOPY
ISHIZUKA, N
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04): : 813 - 826

← 1 2 3 4 5 →