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首页> 外文期刊>Chemistry: A European journal >Regio-and Stereoseletive Reductive Coupling of Bicyclic Alkenes with Propiolates Catalyzed by Nickel Complexes:A Novel Route to Functionalized 1,2-Dihydroarenes and gamma-Lactones
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Regio-and Stereoseletive Reductive Coupling of Bicyclic Alkenes with Propiolates Catalyzed by Nickel Complexes:A Novel Route to Functionalized 1,2-Dihydroarenes and gamma-Lactones

机译：镍配合物催化双环烯烃与丙二酸酯的区域和立体还原还原偶联：一种功能化的1,2-二氢芳烃和γ-内酯的新途径。

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摘要

7-Oxabenzorboranadienes derivatives la-d underwent reductive coupling with alkyl propiolates CH_3 ident to CCO_2CH_3 (2a) PhCident to CCO_2Et (2b) CH_3(CH_2)_3 indent to CCO_2CH_3 (2c) CH_3(CH_2)_4Cindent to CCO_2CH_3 (2d) TMSCindent to CCO_2Et (2e) (CH_3)_3Cident toCCO_2CH_3 (2f) and HCident to CCO_2Et (2g) in the presence of [NiBr_2(dppe)] (deep=Ph_2PCH_2-CH_2PPh_2) H_2O and zine powder in acetonitrile at toom temperature to afford the corresponding 2-alkenyl-1,2-dihydronapthalen-1-ol derivatives 3a-n with remarkabe regio- and diastereose-lectivity in good to excellent yields.Similarly the reaction of 7-azabenzonorbornadienes derivative 1e with propiolates 2a b and d processded smoothly to frrord reductive coupling products 2-alkenyl-1,2-dihydronapthalene carbamates 3o-p in good yields with high regio-and stereoselectivity Thsi nickel catalyzed reductive coupling can be further extended to the reaction of 7-oxdabenzonorornene derivatives Thus 5,6-di(methoxymethyl)-7-oxabicyclo[2.2.1] hept-2-ene (4) reacted with 2a and 2d to furnish cyclohexenol derivatives bearing four cis substituents 5a and b in 81 and 84% yield respectively In contrast to the results of 4 with 2 the resction of dimethyl 7-oxabicyclo[2.2.1]-hept-5-ene-2,3-dicarboxylate (6) with propiolates 2a-b afforded the corresponding reductive coupling/cyclization products bicyclo [3.21] gamma-lactones 7a-d in good yields The reaction provides a convemient one-pot synthesis of gamma-lactones with remarkably high regio- and stereoselectivity.
机译：7-氧苯并硼硼烷二烯衍生物la-d与烷基丙酸酯进行还原偶联，CH_3与CCO_2CH_3（2b）Ph_CCO_2Et（2b）CH_3（CH_2）_3与CCO_2CH_3（2c）CH_3（CH_2）_4与CCO_2CH_3 （2e）（CH_3）_3在[NiBr_2（dppe）]（深= Ph_2PCH_2-CH_2PPh_2）H_2O和锌粉在乙腈中的存在下，于室温下在存在[NiBr_2（dppe）]的情况下向CCO_2CH_3（2f）转移，从HCident到CCO_2Et（2g）。烯基-1,2-二氢萘基-1-醇衍生物3a-n具有很好的区域选择性和非对映选择性，同样，7-氮杂苯并降冰片二烯衍生物1e与丙酸酯2ab和d的反应平稳地进行了frrord还原偶联产物2-烯基-1,2-二氢萘氨基甲酸氨基酯3o-p具有高产率和高区域选择性和立体选择性，该镍催化的还原偶联可以进一步扩展至7-氧代苯并降冰片烯衍生物的反应，因此5,6-二（甲氧基甲基）- 7-氧杂双环[2.2.1]庚-2-烯（4）与2a和2d反应，以81％和84％的产率分别提供带有四个顺式取代基5a和b的环己烯衍生物。与4的结果相比，用2取代二甲基7-氧杂双环[2.2]。 1]-庚烯5,3-二羧酸2,3-二羧酸酯（6）与丙酸酯2a-b以良好的收率提供了相应的还原偶联/环化产物双环[3.21]γ-内酯7a-d反应提供了一种简便的方法-锅合成具有显着高区域选择性和立体选择性的γ-内酯。

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