Diastereoselective Diels-Alder cycloaddition of [(1R)-10-(N,N-diethylsulfamoyl)isobornyl] 2H-azirine to nucleophilic 1,4-disubstituted 1,3-dienes
Diastereoselective Diels-Alder cycloaddition of [(1R)-10-(N,N-diethylsulfamoyl)isobornyl] 2H-azirine to nucleophilic 1,4-disubstituted 1,3-dienes
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DOI：
10.1016/j.tetasy.2009.05.035
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发表时间：
2009-07-02
影响因子：
--
通讯作者：
Duraes, Mario M.
中科院分区：
文献类型：
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作者：
Alves, Maria J.;Costa, Catia;Duraes, Mario M.
手性[（IR）-10-（N，N-二乙基氨磺酰基）异冰片基] 2 H-吖丙啶1 [Timen，A.S.：Somfai，P.J.Org.Chem.2003，9958-9963; Timen，A. S.的; Fisher，A.; Somfai，P. Chem. Commun. 2003，1150-1151]。合成了许多1，4-二取代的-2-氮杂-1，3-二烯2a-g（Alves，M. J.道：Duraes，M. M.; Gil Fortes，A. Tetrahedron 2004，6541-6553]，得到环加合物8a-g，为主要异构体。当R-1，R-2 = At 2a-e时，观察到氮杂环丙烷两个面的高至良好的非对映体区分;当R-1 = Me或H 2f，g时，非对映体选择性急剧下降。氮杂环丙烷1与E，E-1，4-二乙酰氧基-1，3-丁二烯的环加成显示出完全的非对映选择性，得到环加成物11 a。(C)2009爱思唯尔有限公司保留所有权利。
Chiral [(IR)-10-(N,N-diethylsulfamoyl)isobornyl] 2H-azirine 1 [Timen, A.S.: Somfai, P.J. Org. Chem. 2003, 9958-9963; Timen, A. S.; Fisher, A.; Somfai, P. Chem. Commun. 2003, 1150-1151]. was combined to a number of 1,4-disubstituted-2-aza-1,3-dienes 2a-g (Alves, M. J.; Duraes, M. M.; Gil Fortes, A. Tetrahedron 2004, 6541-6553] to give cycloadducts 8a-g as major isomers. High to good diastereofacial differentiation of the two faces of the azirine is observed when R-1,R-2 = At 2a-e; diastereoselectivity drops drastically when R-1 = Me or H 2f,g. Cycloaddition of the azirine 1 to E,E-1,4-diacetoxy-1,3-butadiene shows complete diastereoselectivity giving cycloadduct 11a. (C) 2009 Elsevier Ltd. All rights reserved.