Amine-catalyzed addition of azide ion to α,β-unsaturated carbonyl compounds

被引:83
作者
Guerin, DJ [1 ]
Horstmann, TE [1 ]
Miller, SJ [1 ]
机构
[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA
关键词
D O I
10.1021/ol9909076
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new protocol for the beta-azidation of alpha,beta-unsaturated carbonyl compounds is described, The method employs tertiary amines as catalysts for azide addition. The azide source is a 1:1 mixture of TMSN3 and AcOH. Tertiary amines, either in solution or bound to a solid support, are efficient catalysts for the reaction.
引用
收藏
页码:1107 / 1109
页数:3
相关论文
共 17 条
[1]   Formation of short, stable helices in aqueous solution by β-amino acid hexamers [J].
Appella, DH ;
Barchi, JJ ;
Durell, SR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) :2309-2310
[2]  
Bretherick L., 1975, HDB REACTIVE CHEM HA, P775
[3]   TOTAL SYNTHESIS OF (+)-POLYOXIN-J STARTING FROM MYOINOSITOL [J].
CHIDA, N ;
KOIZUMI, K ;
KITADA, Y ;
YOKOYAMA, C ;
OGAWA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :111-113
[4]  
CHUNG BY, 1988, B KOR CHEM SOC, V9, P269
[5]  
COLE DC, 1994, TETRAHEDRON, V50, P9517
[6]   Minimal acylase-like peptides. Conformational control of absolute stereospecificity [J].
Copeland, GT ;
Jarvo, ER ;
Miller, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6784-6785
[7]   Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts [J].
Ferraris, D ;
Young, B ;
Dudding, T ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4548-4549
[8]  
Gademann K, 1999, ANGEW CHEM INT EDIT, V38, P1223, DOI 10.1002/(SICI)1521-3773(19990503)38:9<1223::AID-ANIE1223>3.0.CO
[9]  
2-A
[10]   VINYLOGOUS POLYPEPTIDES - AN ALTERNATIVE PEPTIDE BACKBONE [J].
HAGIHARA, M ;
ANTHONY, NJ ;
STOUT, TJ ;
CLARDY, J ;
SCHREIBER, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) :6568-6570