A highly enantioselective one-pot sulfur ylide epoxidation reaction

被引：46

作者：

Winn, CL ^{[1
]}

Bellenie, BR ^{[1
]}

Goodman, JM ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 31期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(02)01072-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure tricyclic C-symmetric sulfide I can be prepared in high yield and only three steps from D-mannitol. When used in a one-pot sulfur ylide mediated epoxidation reaction, between 94 and 98% enantiomeric excess was obtained; the highest reported to date for the catalytic process. Molecular modelling studies of the ylide conformation provides a basis for understanding the stereochemical outcome of the reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5427 / 5430

页数：4

共 50 条

[21] In a simple one-pot reaction
Saalfrank, R.W.
Burak, R.
Breit, A.
Stalke, D.
Herbst-Irmer, R.
Daub, J.
Porsch, M.
Bill, E.
Muther, M.
Trautwcin, A.X.
Angewandte Chemie (International Edition in English), 1994, 33 (15-16): : 1621 - 1623
[22] One-Pot Highly Diastereoselective Synthesis of cis-Vinylaziridines via the Sulfur Ylide-Mediated Aziridination and Palladium(0)-Catalyzed Isomerization
Zhu, Ben-Hu
Zheng, Jun-Cheng
Yu, Chang-Bin
Sun, Xiu-Li
Zhou, Yong-Gui
Shen, Qi
Tang, Yong
ORGANIC LETTERS, 2010, 12 (03) : 504 - 507
[23] One-Pot Synthesis of Four Chlorin Derivatives by a Divergent Ylide
Gonzales, Junior
Bhupathiraju, N. V. S. Dinesh K.
Hart, Daniel
Yuen, Man
Sifuentes, Maria Pia
Samarxhiu, Bleron
Maranan, Mark
Berisha, Naxhije
Batteas, James
Drain, Charles Michael
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12): : 6307 - 6314
[24] A simple one-pot, three-component, catalytic, highly enantioselective isoxazolidine synthesis
Rios, Ramon
Ibrahem, Ismail
Vesely, Jan
Zhao, Gui-Ling
Cordova, Armando
TETRAHEDRON LETTERS, 2007, 48 (32) : 5701 - 5705
[25] A Highly Enantioselective One-Pot Synthesis of Spirolactones by an Organocatalyzed Michael Addition/Cyclization Sequence
Sternativo, Silvia
Calandriello, Antonella
Costantino, Ferdinando
Testaferri, Lorenzo
Tiecco, Marcello
Marini, Francesca
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) : 9382 - 9385
[26] Kinugasa Reaction: A Direct One-Pot Route to Highly Functionalized β-Lactams
Khangarot, Rama K.
Kaliappan, Krishna P.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (34) : 7664 - 7677
[27] A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide
Sarabia, Francisco
Chammaa, Samy
Garcia-Castro, Miguel
Martin-Galvez, Francisca
CHEMICAL COMMUNICATIONS, 2009, (38) : 5763 - 5765
[28] Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction
Gommermann, Nina
Knochel, Paul
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) : 4380 - 4392
[29] One-pot highly diastereoselective synthesis of some novel spiro pyrrolizidines via 1,3-dipolar cycloaddition reaction of azomethine ylide
Azizian, J
Karimi, AR
Dastkhan, R
Mohammadi, AA
Mohammadizadeh, MR
JOURNAL OF CHEMICAL RESEARCH-S, 2004, (05): : 347 - 349
[30] One-pot epoxidation of alkenes using aerobic photoperoxidation of toluenes
Taguchi, Miyabi
Nagasawa, Yoshitomo
Yamaguchi, Eiji
Tada, Norihiro
Miura, Tsuyoshi
Itoh, Akichika
TETRAHEDRON LETTERS, 2016, 57 (02) : 230 - 232

← 1 2 3 4 5 →