Synthesis of enantiomerically pure (+)- and (-)-protected 5-aminomethyl-1,3-oxazolidin-2-one derivatives from allylamine and carbon dioxide

被引:22
作者
Fernandez, Isabelle [1 ]
Munoz, Luis [1 ]
机构
[1] Univ Vigo, Fac Quim, Dept Quim Organ, Vigo 36210, Spain
关键词
D O I
10.1016/j.tetasy.2006.08.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The stereoselective synthesis of enantiomerically pure (5R)- and (5S)-aminomethyl-oxazolidinones with different protecting groups have been carried out from an allyl amine as the source of the carbon backbone. The key reaction is the high yield iodiocyclization of enantiomerically pure allylphenethyl amine in the presence of carbon dioxide. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2548 / 2557
页数:10
相关论文
共 25 条
[1]  
ABRAHAM RJ, 2000, J CHEM SOC P2, P803
[2]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[3]   The preparation and first application of a polymer-supported ''Evans'' oxazolidinone. [J].
Allin, SM ;
Shuttleworth, SJ .
TETRAHEDRON LETTERS, 1996, 37 (44) :8023-8026
[4]   A SIMPLE AND GENERAL-ROUTE TO ARYL IODIDES FROM ARENES [J].
BARLUENGA, J ;
CAMPOS, PJ ;
GONZALEZ, JM ;
ASENSIO, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (11) :2623-2624
[5]   ELECTROPHILIC ADDITIONS OF POSITIVE IODINE TO ALKYNES THROUGH AN IODONIUM MECHANISM [J].
BARLUENGA, J ;
RODRIGUEZ, MA ;
CAMPOS, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3104-3106
[6]   Asymmetric alkylations using SuperQuat auxiliaries - an investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones [J].
Bull, SD ;
Davies, SG ;
Jones, S ;
Sanganee, HJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04) :387-398
[7]   Resin type can have important effects on solid phase asymmetric alkylation reactions [J].
Burgess, K ;
Lim, D .
CHEMICAL COMMUNICATIONS, 1997, (08) :785-786
[8]  
CAMPBELL AD, 1998, TETRAHEDRON, V54, P7221
[9]   AN EFFICIENT SYNTHESIS OF (R)-(+)-PROPRANOLOL AND (S)-(-)-PROPRANOLOL FROM RESOLVED 5-IODOMETHYLOXAZOLIDIN-2-ONES [J].
CARDILLO, G ;
ORENA, M ;
SANDRI, S ;
TOMASINI, C .
TETRAHEDRON, 1987, 43 (11) :2505-2512
[10]   A soluble polymer-bound Evans' chiral auxiliary: synthesis, characterization and use in cycloaddition reactions [J].
Desimoni, G ;
Faita, G ;
Galbiati, A ;
Pasini, D ;
Quadrelli, P ;
Rancati, F .
TETRAHEDRON-ASYMMETRY, 2002, 13 (04) :333-337