Hetero-Diels-Alder Reaction of Phosphorylated Nitroso Alkenes with Enol Ethers on Water: A Clean Approach Toward 1,2-Oxazine Derivatives

被引:33
作者
de los Santos, Jesus M. [1 ]
Ignacio, Roberto [1 ]
Es Sbai, Zouhair [1 ]
Aparicio, Domitila [1 ]
Palacios, Francisco [1 ]
机构
[1] Univ Basque Country, Ctr Invest & Estudios Avanzados Lucio Lascaray, Fac Farm, Dept Quim Organ 1, Vitoria 01006, Spain
关键词
ORGANIC-REACTIONS; ASYMMETRIC-SYNTHESIS; 6-SILOXY-SUBSTITUTED 5,6-DIHYDRO-4H-1,2-OXAZINES; ALPHA; BETA-UNSATURATED OXIMES; BETA-AMINOPHOSPHONATES; CONJUGATE PHOSPHINYL; EFFICIENT SYNTHESIS; 4+2 CYCLOADDITIONS; AQUEOUS-MEDIA; CHEMISTRY;
D O I
10.1021/jo501339c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise and eco-friendly synthesis of highly fiinctionalized 1,2-oxazines from phosphinyl- and phosphonyl-nitroso alkenes has been developed. The key step of this process, which involves a two-step sequence of reactions on-water, is a regioselective hetero-Diels Alder cycloaddition reaction of enol ethers to 4-phosphinyl or 4-phosphonyl nitroso alkenes mediated by water itself. The process has also been performed under solvent-free conditions and in organic solvents for comparison.
引用
收藏
页码:7607 / 7615
页数:9
相关论文
共 68 条
[1]  
[Anonymous], 2010, NAME REACTIONS CARBO
[2]  
[Anonymous], 1987, PHOSPHORUS CHEM EVER
[3]  
[Anonymous], BIOMATER SCI
[4]  
Attanasi OA, 2001, HELV CHIM ACTA, V84, P513, DOI 10.1002/1522-2675(20010228)84:2<513::AID-HLCA513>3.0.CO
[5]  
2-S
[6]   Synthesis of an 1-azaglucose analogue with ring-oxygen retained. [J].
Bach, P ;
Bols, M .
TETRAHEDRON LETTERS, 1999, 40 (17) :3461-3464
[7]   Synthesis of novel carbohydrate mimetics via 1,2-oxazines [J].
Bouche, Lea ;
Reissig, Hans-Ulrich .
PURE AND APPLIED CHEMISTRY, 2012, 84 (01) :23-36
[8]   Determining the geometries of transition states by use of antihydrophohic additives in water [J].
Breslow, R .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (07) :471-478
[9]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[10]   SELECTIVE DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTIONS AND SUSPENSIONS [J].
BRESLOW, R ;
MAITRA, U ;
RIDEOUT, D .
TETRAHEDRON LETTERS, 1983, 24 (18) :1901-1904