Lewis acid promoted conjugate addition of vinylmagnesium bromide to chiral alpha,beta-unsaturated N-acyl oxazolidinones

被引：24
作者：
Han, YL [1 ]
Hruby, VJ [1 ]
机构：
[1] UNIV ARIZONA,DEPT CHEM,TUCSON,AZ 85721
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 42期
关键词：
D O I：
10.1016/S0040-4039(97)01777-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lewis acid promoted conjugated additions of vinylmagnesium bromide to chiral alpha,beta-unsaturated N-acyl oxazolidinones are described. A series of enatiomerically pure beta-branched 4-pentenoic acid derivatives have been synthesized with high diastereoselectivity. (C) 1997 Elsevier Science Ltd.
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页码：7317 / 7320
页数：4
相关论文
共 34 条
[1]   ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - SYNTHESIS OF THE OPTICALLY PURE ISOMERS OF INDOLE-PROTECTED BETA-METHYLTRYPTOPHAN SUITABLE FOR PEPTIDE-SYNTHESIS [J].
BOTEJU, LW ;
WEGNER, K ;
HRUBY, VJ .
TETRAHEDRON LETTERS, 1992, 33 (49) :7491-7494
[2]  
BURNER BA, 1984, J AM CHEM SOC, V106, P1865
[3]   EVIDENCE FOR A REVERSIBLE D,PI-STAR-COMPLEXATION, BETA-CUPRATION SEQUENCE IN THE CONJUGATE ADDITION-REACTION OF GILMAN REAGENTS WITH ALPHA-ENONES, BETA-ENONES [J].
COREY, EJ ;
BOAZ, NW .
TETRAHEDRON LETTERS, 1985, 26 (49) :6015-6018
[4]   ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - AN EFFICIENT SYNTHESIS OF OPTICALLY PURE ISOMERS OF BETA-METHYLPHENYLALANINE [J].
DHARANIPRAGADA, R ;
VANHULLE, K ;
BANNISTER, A ;
BEAR, S ;
KENNEDY, L ;
HRUBY, VJ .
TETRAHEDRON, 1992, 48 (23) :4733-4748
[5]   ASYMMETRIC CONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL ALPHA,BETA-UNSATURATED ESTERS [J].
FANG, CL ;
OGAWA, T ;
SUEMUNE, H ;
SAKAI, K .
TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :389-398
[6]   CONFORMATIONAL AND TOPOGRAPHICAL CONSIDERATIONS IN THE DESIGN OF BIOLOGICALLY-ACTIVE PEPTIDES [J].
HRUBY, VJ .
BIOPOLYMERS, 1993, 33 (07) :1073-1082
[7]   EMERGING APPROACHES IN THE MOLECULAR DESIGN OF RECEPTOR-SELECTIVE PEPTIDE LIGANDS - CONFORMATIONAL, TOPOGRAPHICAL AND DYNAMIC CONSIDERATIONS [J].
HRUBY, VJ ;
ALOBEIDI, F ;
KAZMIERSKI, W .
BIOCHEMICAL JOURNAL, 1990, 268 (02) :249-262
[8]   ALPHA-SUBSTITUTION AND GAMMA-SUBSTITUTION REACTIONS OF CYCLIC GAMMA-ACETOXY-ALPHA,BETA-UNSATURATED ESTERS WITH A NOVEL REAGENT BUCU-ALCL3 [J].
IBUKA, T ;
MINAKATA, H .
SYNTHETIC COMMUNICATIONS, 1980, 10 (02) :119-125
[9]   LOCALLY CONSTRAINED TYROSINE ANALOGS WITH RESTRICTED SIDE-CHAIN DYNAMICS [J].
JIAO, D ;
RUSSELL, KC ;
HRUBY, VJ .
TETRAHEDRON, 1993, 49 (17) :3511-3520
[10]   ASYMMETRIC SYNTHESIS WITH SUGAR DERIVATIVES .I. CONJUGATE ADDITIONS OF GRIGNARD REAGENTS TO ALPHA,BETA-UNSATURATED ESTERS OF SUGAR DERIVATIVES [J].
KAWANA, M ;
EMOTO, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1966, 39 (05) :910-+
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