Single-step stereoselective synthesis of (E)- and (Z)-allylamines from acetyl derivatives of Baylis-Hillman adducts

被引:22
作者
Das, B [1 ]
Mahender, G [1 ]
Chowdhury, N [1 ]
Banerjee, J [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
allylamine; Baylis-Hillman adduct; acetyl derivative; NH4OAc; stereochemistry;
D O I
10.1055/s-2005-864822
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoselective synthesis of (E)- and (Z)-allylamines has been achieved in a single-step by treatment of the acetyl derivatives of Baylis-Hillman adducts with ammonium acetate in anhydrous methanol at room temperature. The reaction proceeded under neutral conditions to form the corresponding allylamines in high yields and stereoselectivity.
引用
收藏
页码:1000 / 1002
页数:3
相关论文
共 22 条
[1]   METHYL 4-OXOTHIOLANE-3-CARBOXYLATE AND METHYL 2-METHYL-4-OXOTHIOLANE-3-CARBOXYLATE ANIONS AS SYNTHETIC EQUIVALENTS OF ALPHA-ACRYLATE AND ALPHA-CROTONATE ANIONS - FORMAL SYNTHESIS OF INTEGERRINECIC ACID [J].
BARALDI, PG ;
GUARNERI, M ;
POLLINI, GP ;
SIMONI, D ;
BARCO, A ;
BENETTI, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (11) :2501-2505
[2]   APPLICATIONS OF THE BAYLIS-HILLMAN REACTION-2 - A SIMPLE STEREOSELECTIVE SYNTHESIS OF (E)-TRISUBSTITUTED AND (Z)-TRISUBSTITUTED ALKENES [J].
BASAVAIAH, D ;
SARMA, PKS ;
BHAVANI, AKD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (09) :1091-1092
[3]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[4]  
Baylis A. B, DE Patent, Patent No. 2155113
[5]  
BOCHE G, 1979, TETRAHEDRON LETT, P4967
[6]   ALPHA-METHYLIDENE-BETA-LACTAMS AND ALPHA-ALKYLIDENE-BETA-LACTAMS FROM NONPROTEINOGENIC AMINO-ACIDS [J].
BUCHHOLZ, R ;
HOFFMANN, HMR .
HELVETICA CHIMICA ACTA, 1991, 74 (06) :1213-1220
[7]   Asymmetric synthesis of quaternary α- and β-amino acids and β-lactams via proline-catalyzed Mannich reactions with branched aldehyde donors [J].
Chowdari, NS ;
Suri, JT ;
Barbas, CF .
ORGANIC LETTERS, 2004, 6 (15) :2507-2510
[8]   An efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from unactivated Baylis-Hillman adducts using NaBH4/CuCl2•2H2O [J].
Das, B ;
Banerjee, J ;
Majhi, A ;
Mahender, G .
TETRAHEDRON LETTERS, 2004, 45 (50) :9225-9227
[9]   A simple and facile stereoselective synthesis of (Z)- and (E)-allyl halides catalyzed by silica supported sodium hydrogen sulfate:: factors influencing the yields and stereochemistry of allyl halides [J].
Das, B ;
Banerjee, J ;
Ravindranath, N .
TETRAHEDRON, 2004, 60 (38) :8357-8361
[10]   Organic reactions in water:: An efficient zinc-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes using unactivated alkyl halides [J].
Das, B ;
Banerjee, J ;
Mahender, G ;
Majhi, A .
ORGANIC LETTERS, 2004, 6 (19) :3349-3352