Alkynenitriles: Chelation-controlled conjugate additions

被引:29
作者
Fleming, FF [1 ]
Gudipati, V [1 ]
Steward, OW [1 ]
机构
[1] Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA
关键词
D O I
10.1021/ol017286c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Chelation between gamma-hydroxybutynenitrile and Grignard reagents triggers a particularly facile anionic conjugate addition reaction. Structurally diverse Grignard reagents add with equal efficiency, providing an intermediate anion that stereoselectively alkylates benzaldehyde in an overall addition-alkylation reaction.
引用
收藏
页码:659 / 661
页数:3
相关论文
共 23 条
[1]   PROSTAGLANDINS AND CONGENERS .28. SYNTHESIS OF 2-(OMEGA-CARBALKOXYALKYL)CYCLOPENT-2-EN-1-ONES, INTERMEDIATES FOR PROSTAGLANDIN SYNTHESES [J].
BERNADY, KF ;
POLETTO, JF ;
NOCERA, J ;
MIRANDO, P ;
SCHAUB, RE ;
WEISS, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4702-4715
[2]  
EARL RA, 1981, ORG SYNTH, V60, P81
[3]   Metal mediated carbometallation of alkynes and alkenes containing adjacent heteroatoms [J].
Fallis, AG ;
Forgione, P .
TETRAHEDRON, 2001, 57 (28) :5899-5913
[4]   γ-hydroxy unsaturated nitriles:: Chelation-controlled conjugate additions [J].
Fleming, FF ;
Wang, QZ ;
Steward, OW .
ORGANIC LETTERS, 2000, 2 (10) :1477-1479
[5]   Unsaturated nitriles: Conjugate addition-silylation with Grignard reagents [J].
Fleming, FF ;
Pu, YF ;
Tercek, F .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4883-4885
[6]   ALPHA,BETA-UNSATURATED NITRILES - AN EFFICIENT CONJUGATE ADDITION WITH POTASSIUM BENZENESELENOLATE AND POTASSIUM BENZENESULFENYLATE [J].
FLEMING, FF ;
PAK, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4299-4301
[7]   alpha,beta-Unsaturated nitriles: Stereoselective conjugate addition reactions [J].
Fleming, FF ;
Hussain, Z ;
Weaver, D ;
Norman, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1305-1309
[8]   Magnesium mediated carbometallation of propargyl alcohols: direct routes to dihydroxydienes and enediyne alcohols [J].
Forgione, P ;
Fallis, AG .
TETRAHEDRON LETTERS, 2000, 41 (01) :11-15
[9]   SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS [J].
HOVEYDA, AH ;
EVANS, DA ;
FU, GC .
CHEMICAL REVIEWS, 1993, 93 (04) :1307-1370
[10]   Selective halogen-magnesium exchange reaction via organomagnesium ate complex [J].
Inoue, A ;
Kitagawa, K ;
Shinokubo, H ;
Oshima, K .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4333-4339