Recent advances and applications in asymmetric aza-Michael addition chemistry

被引:175
作者
Krishna, Palakodety Radha [1 ]
Sreeshailam, Aare [1 ]
Srinivas, Ravula [1 ]
机构
[1] Indian Inst Chem Technol, Discovery Lab, Div Organ Chem 3, Hyderabad 500607, Andhra Pradesh, India
关键词
Diastereoselective aza-Michael addition; Enantioselective aza-Michael addition; Double aza-Michael addition; BETA-AMINO ACIDS; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; ENANTIOSELECTIVE CONJUGATE ADDITION; CHIRAL AMMONIA EQUIVALENT; ALKENOYL-N-OXAZOLIDINONES; ALPHA-HYDROXY ACIDS; STEREOSELECTIVE-SYNTHESIS; AROMATIC-AMINES; LITHIUM (ALPHA-METHYLBENZYL)ALLYLAMIDE; O-BENZYLHYDROXYLAMINE;
D O I
10.1016/j.tet.2009.08.021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:9657 / 9672
页数:16
相关论文
共 99 条
[1]   LEWIS ACID-PROMOTED 1,4-ADDITION TO CHIRAL IMIDE DERIVATIVES IN THE SYNTHESIS OF BETA-AMINO ACIDS [J].
AMOROSO, R ;
CARDILLO, G ;
SABATINO, P ;
TOMASINI, C ;
TRERE, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5615-5619
[2]   Highly diastereoselective conjugate addition of lithium dialkylamides to alpha,beta-unsaturated esters having a chiral center at the gamma-position [J].
Asao, N ;
Shimada, T ;
Sudo, T ;
Tsukada, N ;
Yazawa, K ;
Gyoung, YS ;
Uyehara, T ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6274-6282
[3]   Li3[Ln(binol)3]•6THF:: New anhydrous lithium lanthanide binaphtholates and their use in enantioselective alkyl addition to aldehydes [J].
Aspinall, HC ;
Dwyer, JLM ;
Greeves, N ;
Steiner, A .
ORGANOMETALLICS, 1999, 18 (08) :1366-1368
[4]   A GENERAL PROCEDURE FOR THE SYNTHESIS OF ISOXAZOLIDIN-5-ONES [J].
BALDWIN, JE ;
HARWOOD, LM ;
LOMBARD, MJ .
TETRAHEDRON, 1984, 40 (21) :4363-4370
[5]   ASYMMETRIC-SYNTHESIS WITH CHIRAL HYDROXYLAMINES - SYNTHESIS OF OPTICALLY PURE 4-SUBSTITUTED AZETIDINONES [J].
BALDWIN, SW ;
AUBE, J .
TETRAHEDRON LETTERS, 1987, 28 (02) :179-182
[6]   Synthesis of enantiomerically pure aziridine-2-imides by cyclization of chiral 3′-benzyloxyamino imide enolates [J].
Bongini, A ;
Cardillo, G ;
Gentilucci, L ;
Tomasini, C .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9148-9153
[7]   Asymmetric synthesis of N-protected syn and anti (E)-3-amino-2-hydroxy-4-hexenoate:: A practical method for the C-α epimerization of anti β-amino-α-hydroxy acids [J].
Brackenridge, I ;
Davies, SG ;
Fenwick, DR ;
Ichihara, O ;
Polywka, MEC .
TETRAHEDRON, 1999, 55 (02) :533-540
[8]  
Bull SD, 2000, SYNLETT, P1257
[9]   ASYMMETRIC-SYNTHESIS OF BETA-AMINO-ALPHA-HYDROXY ACIDS VIA DIASTEREOSELECTIVE HYDROXYLATION OF HOMOCHIRAL BETA-AMINO ENOLATES [J].
BUNNAGE, ME ;
CHERNEGA, AN ;
DAVIES, SG ;
GOODWIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17) :2373-2384
[10]   MICHAEL-TYPE ADDITION OF PHTHALIMIDE SALTS TO CHIRAL ALPHA,BETA-UNSATURATED IMIDES [J].
CARDILLO, G ;
DESIMONE, A ;
GENTILUCCI, L ;
SABATINO, P ;
TOMASINI, C .
TETRAHEDRON LETTERS, 1994, 35 (28) :5051-5054