One-pot synthesis of chiral multifunctionalized aziridines

被引：15
作者：
Fioravanti, Stefania [1 ]
Morea, Sara [1 ]
Morreale, Alberto [1 ]
Pellacani, Lucio [1 ]
Tardella, Paolo A. [1 ]
机构：
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
来源：
TETRAHEDRON | 2009年 / 65卷 / 02期
关键词：
Michael addition; Amination; Asymmetric induction; Heterocycles; DIASTEREOSELECTIVE CYCLOPROPANATION; KNOEVENAGEL CONDENSATION; ASYMMETRIC-SYNTHESIS; HOMOCHIRAL KETALS; DIMETHYLZINC;
D O I：
10.1016/j.tet.2008.11.017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct synthetic procedure to obtain chiral aziridines is reported, involving a diastereoselective aza-MIRC (Michael Initiated Ring Closure) reaction. Multifunctionalized aziridines are obtained in high overall yields (82-92%) and with a diastereomeric ratio up to 99:1. Further synthetic elaboration can lead to the formation of interesting biochemical molecules, such as amino glycosides. The diastereomeric induction seems to be strongly controlled both by the choice of chiral moiety and by the electron withdrawing groups (EWG) present on the starting alkenes. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：484 / 488
页数：5
相关论文
共 29 条
[1]   Asymmetric radical addition of ethers to enantiopure N-p-toluenesulfinyl aldimines, mediated by dimethylzinc-air [J].
Akindele, Tito ;
Yamamoto, Yasutomo ;
Maekawa, Masaru ;
Umeki, Hiroyuki ;
Yamada, Ken-ichi ;
Tomioka, Kiyoshi .
ORGANIC LETTERS, 2006, 8 (25) :5729-5732
[2]   Synthesis of substituted stilbenes via the Knoevenagel condensation [J].
Al-Shihry, SS .
MOLECULES, 2004, 9 (08) :658-665
[3]  
ANDERSEN NH, 1977, TETRAHEDRON LETT, P3783
[4]   Efficient synthesis of 4-cyano 2,3-dihydrooxazoles by direct amination of 2-alkylidene 3-oxo nitriles [J].
Burini, E ;
Fioravanti, S ;
Morreale, A ;
Pellacani, L ;
Tardella, PA .
SYNLETT, 2005, (17) :2673-2675
[5]   Aza-Michael addition of nosyloxycarbamates to 2-(trifluoromethyl)acrylates [J].
Colantoni, D ;
Fioravanti, S ;
Pellacani, L ;
Tardella, PA .
ORGANIC LETTERS, 2004, 6 (02) :197-200
[6]   (S,S)-(+)-pseudoephedrine as chiral auxiliary in asymmetric aza-michael reactions.: Unexpected selectivity change when manipulating the structure of the auxiliary [J].
Etxebarria, J ;
Vicario, JL ;
Badia, D ;
Carrillo, L ;
Ruiz, N .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) :8790-8800
[7]   A FACILE AZIRIDINATION OF ALLYLIC AND HOMOALLYLIC CYCLIC ACETALS [J].
FIORAVANTI, S ;
LORETO, MA ;
PELLACANI, L ;
TARDELLA, PA .
TETRAHEDRON LETTERS, 1993, 34 (27) :4353-4354
[8]   Cinchona alkaloids in the asymmetric synthesis of 2-(phenylsulfanyl)aziridines [J].
Fioravanti, S ;
Mascia, MG ;
Pellacani, L ;
Tardella, PA .
TETRAHEDRON, 2004, 60 (37) :8073-8077
[9]   Synthesis of N-protected cyano aziridines [J].
Fioravanti, S ;
Morreale, A ;
Pellacani, L ;
Tardella, PA .
SYNLETT, 2004, (06) :1083-1085
[10]   Solution-phase synthesis of 2-cyano and 2-amido aziridinyl peptides [J].
Fioravanti, Stefania ;
Massari, Davide ;
Morreale, Alberto ;
Pellacani, Lucio ;
Tardella, Paolo A. .
TETRAHEDRON, 2008, 64 (14) :3204-3211
123