Hindered Bronsted bases as Lewis base catalysts

被引:18
作者
Tabassum, Sobia [1 ]
Sereda, Oksana [1 ]
Reddy, Peddiahgari Vasu Govardhana [1 ]
Wilhelm, Rene [1 ]
机构
[1] Clausthal Univ Technol, Inst Organ Chem, D-38678 Clausthal Zellerfeld, Germany
关键词
CARBONYLVERBINDUNGEN MIT SAURECHLORIDEN; KETENE-IMINE CYCLOADDITION; GEGENWART TERTIARER AMINE; N-HETEROCYCLIC CARBENES; BETA-LACTAMS; ASYMMETRIC-SYNTHESIS; STAUDINGER REACTION; SODIUM BIS(TRIMETHYLSILYL)AMIDE; DISUBSTITUTED KETENES; ENANTIOSELECTIVE SYNTHESIS;
D O I
10.1039/b908899g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
KHMDS and KOtBu are well established as strong, hindered, non-nucleophilic Bronsted bases. However, in the present work these bases are applied as highly active Lewis base catalysts for the formal [2+2] cycloaddition of ketenes with aldehydes and imines.
引用
收藏
页码:4009 / 4016
页数:8
相关论文
共 73 条
[1]   A convenient trans-stereoselective synthesis of phenanthridine derived 2-azetidinones using the Staudinger ketene-imine cycloaddition [J].
Alcaide, B ;
Rodríguez-Vicente, A .
TETRAHEDRON LETTERS, 1999, 40 (10) :2005-2006
[2]   Spiro β-lactams as β-turn mimetics.: Design, synthesis, and NMR conformational analysis [J].
Alonso, E ;
López-Ortiz, F ;
del Pozo, C ;
Peralta, E ;
Macías, A ;
González, J .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6333-6338
[3]  
ASTRUC D, 2006, ARKIVOC, V173
[4]   STEREOSPECIFIC FORMATION OF ENOLATES FROM REACTION OF UNSYMMETRICAL KETENES AND ORGANO-LITHIUM REAGENTS [J].
BAIGRIE, LM ;
SEIKLAY, HR ;
TIDWELL, TT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5391-5396
[5]   Stereoselective synthesis of β-lactams with polyaromatic imines:: Entry to new and novel anticancer agents [J].
Banik, I ;
Becker, FF ;
Banik, BK .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (01) :12-15
[6]  
BENTELY PH, 1993, RECENT ADV CHEM ANTI
[7]   A SIMPLE SYNTHESIS OF PRIMARY AMINES VIA THEIR N,N-BIS(TRIMETHYLSILYL) DERIVATIVES [J].
BESTMANN, HJ ;
WOLFEL, G .
CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (03) :1250-1254
[8]   β-Lactones as Specific Inhibitors of CIpP Attenuate the Production of Extracellular Virulence Factors of Staphylococcus aureus [J].
Boettcher, Thomas ;
Sieber, Stephan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14400-+
[9]   UBER DIE UMSETZUNG VON CARBONYLVERBINDUNGEN MIT SAURECHLORIDEN IN GEGENWART TERTIARER AMINE .2. OPTISCH AKTIVE BETA-LACTONE [J].
BORRMANN, D ;
WEGLER, R .
CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (05) :1575-&
[10]   UBER DIE UMSETZUNG VON CARBONYLVERBINDUNGEN MIT SAURECHLORIDEN IN GEGENWART TERTIARER AMINE [J].
BORRMANN, D ;
WEGLER, R .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (04) :1245-&