Diastereoselective aziridination of chiral α-carbonyl enoates

被引:28
作者
Fioravanti, S [1 ]
Morreale, A [1 ]
Pellacani, L [1 ]
Tardella, PA [1 ]
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
关键词
D O I
10.1021/jo025670x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nosyloxycarbamates very efficiently aziridinate optically active a-carbonyl enoates with high levels of diastereoselectivity under mild conditions and in a straightforward process.
引用
收藏
页码:4972 / 4974
页数:3
相关论文
共 28 条
[11]   Aziridination of α,β-unsaturated ketones [J].
Fioravanti, S ;
Pellacani, L ;
Tabanella, S ;
Tardella, PA .
TETRAHEDRON, 1998, 54 (46) :14105-14112
[12]   ASYMMETRIC-SYNTHESIS OF BETA-SUBSTITUTED ALCANOIC ACIDS VIA HIGHLY STEREOSELECTIVE CONJUGATE ADDITIONS OF ORGANOCOPPER COMPOUNDS TO CHIRAL ENOATES [J].
HELMCHEN, G ;
WEGNER, G .
TETRAHEDRON LETTERS, 1985, 26 (49) :6051-6054
[13]   Total synthesis of natural (+)-FR900482 .1. Synthetic and end-game strategies [J].
Katoh, T ;
Itoh, E ;
Yoshino, T ;
Terashima, S .
TETRAHEDRON LETTERS, 1996, 37 (20) :3471-3474
[14]   Trifluoromethanesulfonic acid, an unusually powerful catalyst for the Michael addition reaction of β-ketoesters under solvent-free conditions [J].
Kotsuki, H ;
Arimura, K ;
Ohishi, T ;
Maruzasa, R .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3770-3773
[15]   CARBETHOXYNITRENE BY ALPHA-ELIMINATION . REACTIONS WITH HYDROCARBONS [J].
LWOWSKI, W ;
MARICICH, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (16) :3630-&
[16]   Recent synthetic applications of chiral aziridines [J].
McCoull, W ;
Davis, FA .
SYNTHESIS-STUTTGART, 2000, (10) :1347-1365
[17]   Induction of p53 by the concerted actions of aziridine and quinone moieties of diaziquone [J].
Ngo, EO ;
Nutter, LM ;
Sura, T ;
Gutierrez, PL .
CHEMICAL RESEARCH IN TOXICOLOGY, 1998, 11 (04) :360-368
[18]   The asymmetric synthesis of aziridines [J].
Osborn, HMI ;
Sweeney, J .
TETRAHEDRON-ASYMMETRY, 1997, 8 (11) :1693-1715
[19]   DIASTEREOSELECTIVE STEREODIVERGENT ADDITION OF E-CROTYLSILANES AND Z-CROTYLSILANES TO 2-CYCLOPENTENONE DERIVATIVES WITH CHIRAL AUXILIARIES AT 2-POSITION [J].
PAN, LR ;
TOKOROYAMA, T .
TETRAHEDRON LETTERS, 1992, 33 (11) :1469-1472
[20]   ORGANOSELENIUM CHEMISTRY - CONVERSION OF KETONES TO ENONES BY SELENOXIDE SYN ELIMINATION [J].
REICH, HJ ;
RENGA, JM ;
REICH, IL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (19) :5434-5447