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首页> 外文期刊>Chemistry: A European journal >Regio- and stereoselective 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 stereoselective reductive coupling of bicyclic alkenes with propiolates catalyzed by nickel complexes: A novel route to functionalized 1,2-dihydroarenes and gamma-lactones

机译：镍配合物催化的双环烯烃与丙酸酯的区域和立体选择性还原偶联：官能化1,2-二氢芳烃和γ-内酯的新途径

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7-Oxabenzonorbornadienes derivatives 1a-d underwent reductive coupling with alkyl propiolates CH,(-CCO2CH3 (2a), PhCdropCCO(2)Et (2b), CH3(CH2)(3)CdropCCO(2)CH(3) (2c), CH3(CH2)(3)(CdropCO(2)CH(3) (2d), TMSCdropCCO(2)Et (2e), (CH3)(3)CdropCCO(2)CH(3) (2f) and HC-CCO2Et (2g) in the presence of [NiBr2(dppe)] (dppe=Ph(2)pCH(2)CH(2)PPh(2)), H2O and zinc powder in acetonitrile at room temperature to afford the corresponding 2-alkenyl-1,2dihydronapthalen-1-ol derivatives 3a - n with remarkable regio- and diastereoselectivity in good to excellent yields. Similarly, the reaction of 7-azabenzonorbornadienes derivative le with propiolates 2 a, b and d proceeded smoothly to afford reductive coupling products 2-alkenyl-1,2-dihydronapthalene carbamates 3o-p in good yields with high regio- and stereoselectivity. This nickel-catalyzed reductive coupling can be further extended to the reaction of 7-oxabenzonorbornene derivatives. Thus, 5,6-di(methoxymethyl)-7-oxabicy-clo[2.2.1]hept-2-ene (4) reacted with 2a and 2d to furnish cyclohexenol derivatives bearing four cis substituents 5 a and b in 81 and 84% yield, respectively. In contrast to the results of 4 with 2, the reaction of dimethyl 7-oxabicyclo[2.2.1]-hept-5-ene-2,3-dicarboxylate (6) with propiolates 2a-d afforded the corresponding reductive coupling/cyclization products, bicyclo[3.2.1]gamma-lactones 7a-d in good yields. The reaction provides a convenient one-pot synthesis of gamma-lactones with remarkably high regio- and stereoselectivity. [References: 58]
机译：7-氧苯并降冰片二烯衍生物1a-d与丙酸烷基酯CH，（-CCO2CH3（2a），PhCdropCCO（2）Et（2b），CH3（CH2）（3）CdropCCO（2）CH（3）（2c），进行还原偶联CH3（CH2）（3）（CdropCO（2）CH（3）（2d），TMSCdropCCO（2）Et（2e），（CH3）（3）CdropCCO（2）CH（3）（2f）和HC-CCO2Et （2g）在[NiBr2（dppe）]（dppe = Ph（2）pCH（2）CH（2）PPh（2）），H2O和锌粉在室温下于乙腈存在的条件下提供相应的2-烯基-1,2二氢萘基-1-醇衍生物3a-n具有显着的区域选择性和非对映选择性，并具有良好的收率，同样，7-氮杂苯并降冰片二烯衍生物le与丙酸酯2a，b和d的反应进展顺利，得到还原偶联产物2 -烯基-1,2-二氢萘氨基甲酸酯3o-p的收率高，具有较高的区域和立体选择性，这种镍催化的还原偶联作用可进一步扩展至7-氧杂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-clo [2.2.1]庚-2-烯（4）反应后2a和2d分别提供具有四个顺式取代基5a和b的环己烯衍生物，产率为81％和84％。与4与2的结果相反，7-氧杂双环[2.2.1]-庚-5-烯-2,3-二羧酸二甲酯（6）与丙酸酯2a-d的反应提供了相应的还原偶联/环化产物，双环[3.2.1]γ-内酯7a-d，收率良好。该反应提供了方便的一锅合成的γ-内酯，具有很高的区域选择性和立体选择性。 [参考：58]

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