A catalytic enantioselective aza-Michael reaction:: Novel protocols for asymmetric synthesis of β-amino carbonyl compounds

被引:275
作者
Xu, LW [1 ]
Xia, CG [1 ]
机构
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
关键词
asymmetric synthesis; aza-Michael reaction; conjugate addition; beta-amino carbonyl compound;
D O I
10.1002/ejoc.200400619
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Amino carbonyl functionalities are ubiquitous motifs in natural and nonnatural products such as alkaloids and polyketides. Among the reactions for the synthesis of beta-amino carbonyl compounds and beta-substituted beta-amino acids, aza-Michael reactions using catalytic amounts of chiral Lewis acids might provide the best methods for the generation of optically active beta-amino carbonyl compounds. During the last five years, the asymmetric aza-Michael reaction has emerged as a very powerful tool for the synthesis of chiral beta-amino carbonyl compounds, as will be discussed in this microreview. (C) Wiley-VCH Verlag GmbH Co.
引用
收藏
页码:633 / 639
页数:7
相关论文
共 70 条
[1]  
Abele S, 2000, EUR J ORG CHEM, V2000, P1
[2]  
Bull SD, 2000, SYNLETT, P1257
[3]   Hydroamination of alkynes catalyzed by a cationic rhodium(I) complex [J].
Burling, S ;
Field, LD ;
Messerle, BA .
ORGANOMETALLICS, 2000, 19 (01) :87-90
[4]   Lewis acid-promoted synthesis and reactivity of β-O-benzylhydroxylamino imides derived from D-glyceraldehyde [J].
Cardillo, G ;
Gentilucci, L ;
De Matteis, V .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :5957-5962
[5]   Enantioselective synthesis of aziridine 2,2-dicarboxylates. Part 1: Copper(II)-bisoxazoline complex-catalysed Michael reaction on alkylidene malonates [J].
Cardillo, G ;
Fabbroni, S ;
Gentilucci, L ;
Gianotti, M ;
Perciaccante, R ;
Tolomelli, A .
TETRAHEDRON-ASYMMETRY, 2002, 13 (13) :1407-1410
[6]   ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ESTERS THROUGH HIGH-PRESSURE-INDUCED ADDITION OF AMINES TO ALPHA,BETA-ETHYLENIC ESTERS [J].
DANGELO, J ;
MADDALUNO, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8112-8114
[7]   Chiral ligand-controlled asymmetric conjugate addition of lithium amides to enoates [J].
Doi, H ;
Sakai, T ;
Iguchi, M ;
Yamada, K ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2886-2887
[8]   The [IrCl(diphosphine)](2)/fluoride system. Developing catalytic asymmetric olefin hydroamination [J].
Dorta, R ;
Egli, P ;
Zurcher, F ;
Togni, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10857-10858
[9]   Asymmetric synthesis of β-amino cyclohexyl sulfonates, β-sultams and γ-sultones [J].
Enders, D ;
Wallert, S ;
Runsink, J .
SYNTHESIS-STUTTGART, 2003, (12) :1856-1868
[10]  
Enders D, 2002, SYNLETT, P304