Efficient nitro-aldol reaction using SmI2:: A new route to nitro alcohols under very mild conditions

被引:29
作者
Concellon, Jose M. [1 ]
Rodriguez-Solla, Humberto [1 ]
Concellon, Carmen [1 ]
机构
[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain
关键词
D O I
10.1021/jo061465w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(Chemical Equation Presented) A novel method to obtain racemic 1-nitroalkan-2-ols by reaction of bromonitromethane with a variety of aldehydes and promoted by SmI2 is reported. On the basis of these results, the chiral version has also been performed with chiral N,N-dibenzyl amino aldehydes, affording the corresponding enantiopure 3-amino-1-nitroalkan-2-ols with good stereoselectivity. © 2006 American Chemical Society.
引用
收藏
页码:7919 / 7922
页数:4
相关论文
共 48 条
[1]   SYNTHESIS OF POLYNITROADAMANTANES - OXIDATIONS OF OXIMINOADAMANTANES [J].
ARCHIBALD, TG ;
BAUM, K .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4645-4649
[2]   Easy access to (E,Z)-β-nitro-α,β-olefinated hydrazones, 6-oxo-1,6-dihydropyridazines, and 4-chloro-1-aminopyrroles by domino reactions of 1,2-diaza-1,3-butadienes with halogen-coactivated methylene or methine compounds [J].
Attanasi, OA ;
Ballini, R ;
De Crescentini, L ;
Filippone, P ;
Mantellini, F .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9653-9657
[3]   A one pot, solvent-free synthesis of acyclic α-nitro ketones through the nitroaldol reaction [J].
Ballini, R ;
Bosica, G ;
Parrini, M .
TETRAHEDRON LETTERS, 1998, 39 (43) :7963-7964
[4]   A general procedure for the one-pot preparation of polyfunctionalized nitrocyclopropanes [J].
Ballini, R ;
Fiorini, D ;
Palmieri, A .
SYNLETT, 2003, (11) :1704-1706
[5]   β-Elimination reactions by using samarium diiodide [J].
Concellón, JM ;
Rodríguez-Solla, H .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :599-609
[6]   Total regioselective and diastereospecific iodolysis of 2,3-epoxyamides promoted by SMI2:: Synthesis of (2R*,3R*)- or (2R*,3S*)-2-hydroxy-3-iodoamides [J].
Concellón, JM ;
Bardales, E ;
Concellón, C ;
García-Granda, S ;
Díaz, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) :6923-6926
[7]   Synthesis of (E)-α-hydroxy-β,γ-unsaturated amides with high selectivity from α,β-epoxyamides by using catalytic samarium diiodide or triiodide [J].
Concellón, JM ;
Bernad, PL ;
Bardales, E .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (10) :2445-2450
[8]   Very rapid preparation of SmI2 by sonic treatment of iodoform and metallic samarium [J].
Concellón, JM ;
Rodríguez-Solla, H ;
Bardales, E ;
Huerta, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (09) :1775-1778
[9]  
Corey EJ, 1999, ANGEW CHEM INT EDIT, V38, P1931, DOI 10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO
[10]  
2-4