A general method for the vinylation of nitrones.: Synthesis of allyl hydroxylamines and allyl amines

被引:23
作者
Merino, P [1 ]
Anoro, S [1 ]
Franco, S [1 ]
Gascon, JM [1 ]
Martin, V [1 ]
Merchan, FL [1 ]
Revuelta, J [1 ]
Tejero, T [1 ]
Tuñon, V [1 ]
机构
[1] Univ Zaragoza, Fac Ciencias, Dept Quim Organ, ICMA, E-50009 Aragon, Spain
关键词
D O I
10.1080/00397910008087449
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.
引用
收藏
页码:2989 / 3021
页数:33
相关论文
共 80 条
[1]   Enantioselective synthesis of (S)-Vigabatrin(R) [J].
Alcon, M ;
Poch, M ;
Moyano, A ;
Pericas, MA ;
Riera, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (17) :2967-2974
[2]   A CONCISE ENANTIOSELECTIVE SYNTHESIS OF ALLYLAMINES AND N-BOC-BETA-AMINO ACIDS [J].
ALCON, M ;
CANAS, M ;
POCH, M ;
MOYANO, A ;
PERICAS, MA ;
RIERA, A .
TETRAHEDRON LETTERS, 1994, 35 (10) :1589-1592
[3]   On the stereoselectivity of reactions of alkoxyallylstannanes and alkoxy aldehydes [J].
Almendros, P ;
Thomas, EJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (17) :2561-2568
[4]  
Alvaro G, 1998, SYNTHESIS-STUTTGART, P1773
[5]   Aza-Claisen rearrangement: Synthesis of 5'-branched 5'-aminothymidines [J].
Ammenn, J ;
Altmann, KH ;
Bellus, D .
HELVETICA CHIMICA ACTA, 1997, 80 (05) :1589-1606
[6]   Diastereoselective addition of higher order cuprates and zinc-copper reagents to imines derived from (S)-1-phenylethylamine [J].
Bandini, M ;
Cozzi, PG ;
Umani-Ronchi, A ;
Villa, M .
TETRAHEDRON, 1999, 55 (26) :8103-8110
[7]   ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC AMINES BY ADDITION OF ALLYLMETAL REAGENTS TO IMINES DERIVED FROM (S)-VALINE ESTERS [J].
BASILE, T ;
BOCOUM, A ;
SAVOIA, D ;
UMANIRONCHI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7766-7773
[8]   A NEW ALPHA-SELECTIVE SYNTHETIC EQUIVALENT FOR THE CROTYL ANION IN ADDITIONS TO IMINES [J].
BETZ, J ;
HEUSCHMANN, M .
TETRAHEDRON LETTERS, 1995, 36 (23) :4043-4046
[9]  
BROWN DS, 1995, TETRAHEDRON, V51, P11473
[10]   Asymmetric synthesis of anti-convulsive drug (S)-Vigabatrin® [J].
Chandrasekhar, S ;
Mohapatra, S .
TETRAHEDRON LETTERS, 1998, 39 (35) :6415-6418