Intermolecular nitroso Diels-Alder cycloaddition of α-acetoxynitroso derivatives in aqueous medium

被引:29
作者
Calvet, G [1 ]
Guillot, R [1 ]
Blanchard, N [1 ]
Kouklovsky, C [1 ]
机构
[1] Inst Chim Mol & Mat Orsay, UMR CNRS 8615, Lab Synth Subst Nat, F-91400 Orsay, France
关键词
D O I
10.1039/b513397a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Diels-Alder cycloadditions of the alpha-acetoxynitroso dienophile 1 in water are reported. The rapid and high yielding synthesis of structurally diverse 3,6-dihydro-1,2-oxazines complements the straightforward elaboration of aminoalcohols obtained from the alpha-acetoxynitroso derivative 1 in anhydrous medium. A rationale for this solvent-dependent product distribution is proposed.
引用
收藏
页码:4395 / 4401
页数:7
相关论文
共 62 条
[1]  
AMROLLAHMADJDABADI A, 1986, SYNTHESIS-STUTTGART, P826
[2]   REGIOCHEMICAL AND STEREOCHEMICAL VARIATIONS IN DIELS-ALDER REACTIONS [J].
ARSENIYADIS, S ;
RODRIGUEZ, R ;
YASHUNSKY, DV ;
CAMARA, J ;
OURISSON, G .
TETRAHEDRON LETTERS, 1994, 35 (27) :4843-4846
[3]   Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine [J].
Baldwin, SW ;
Debenham, JS .
ORGANIC LETTERS, 2000, 2 (02) :99-102
[4]  
BELETSKAYA IP, 1983, AMBIDENT ANIONS, P176
[5]   ENHANCED HYDROGEN-BONDING OF WATER TO DIELS-ALDER TRANSITION-STATES - AB-INITIO EVIDENCE [J].
BLAKE, JF ;
LIM, D ;
JORGENSEN, WL .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :803-805
[6]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[7]   Lewis acid-promoted hetero Diels-Alder cycloaddition of α-acetoxynitroso dienophiles [J].
Calvet, G ;
Dussaussois, M ;
Blanchard, N ;
Kouklovsky, C .
ORGANIC LETTERS, 2004, 6 (14) :2449-2451
[8]  
CALVET G, 2005, SYNTHESIS
[9]   Solvent effects on Diels-Alder reactions. The use of aqueous mixtures of fluorinated alcohols and the study of reactions of acrylonitrile [J].
Cativiela, C ;
Garcia, JI ;
Gil, J ;
Martinez, RM ;
Mayoral, JA ;
Salvatella, L ;
Urieta, JS ;
Mainar, AM ;
Abraham, MH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (03) :653-660
[10]   Modelling of solvent effects on the Diels-Alder reaction [J].
Cativiela, C ;
Garcia, JI ;
Mayoral, JA ;
Salvatella, L .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (03) :209-&