11联萘22二胺的合成及在不对称合成中的应用

2003231,3743ChineseJournalofOrganicChemistryVol.23,2003No.1,37431,1222,22X,a,bcabX(a050091)(b071002)(c050091)1,1222,22(),Diels2Alder.1,1222,22,,,PreparationandApplicationinAsymmetricalSynthesisof2,22Diamino21,12binaphthaleneZHANG,Zhan2HuiX,a,bMO,Li2PingcLIU,Qing2BinaLI,Tong2Shuangb(aInstituteofChemistryandChemicalEngineering,HebeiNormalUniversity,Shijiazhuang050091)(bCollegeofChemistryandEnvironmentalScience,HebeiUniversity,Baoding071002)(cCollegeofChemistry,HebeiNormalUniversity,Shijiazhuang050091)AbstractThispaperpresentsabriefreviewofpreparationof2,22diamino21,12binaphthalenecompoundsandoutlinestheprogressintheirapplicationasachiralauxiliaryoraligandintheasymmetrichydrogenationofalkenes,ketonesandimines,andintheasymmetriccyclopanationofolefins,alkylationandallylationofaldehydes,allylicsubstitutionandenantioselectiveDiels2Alderreaction.Keywords2,22diamino21,12binaphthalene,preparation,application,asymmetricalsynthesis1,12C2[1].C2,.1,1222,22(BINOL,,1)[2],1,1222,22(BINAS,2)[3]1,1222,22(BINAM,,3).,..11.12222(4)(4878h)3,(36%55%),(170180),[46],3.1.22222(5),Na2SO32,22(6),SnCl2[7]Zn2NH4Cl[10,11](7),[12]3,70%87%.XE2mail:[e-mail]15,2002;revisedMay14,2002;acceptedMay23,2002.(No.29872011)(No.L2000q16).1.322Smrcina[13](3).22(5)CuCl222h,58%(3),CuCl234%.22(4)22(5)11CuCl2290282222221,12(8)(3)(1).22(4)22(5)CH2Cl2,FeCl348h,8,3179129[14].22(5)22232CuCl24H2O2,15%2,2223221,12[15].[16]/22(3),8h,65%.,CuCl22H2O,FeCl32H2O,CuCl22CH3OH,Ce(NH4)4(SO4)42H2O2C6H6Fe(acac)32toluene,22(3).22,,.,22,(3).[17],(3).22CuCl22H2O112CuCl2.,,(3),56%.,,,.2(3),.(3).2.1,,,.:(R,S)23CH2Cl2d2(+)22102,,,,,,,(R)23,99.7%,99%ee.CH2Cl2,,,,,,(S)23,72%,99%ee[10]..2.2,.83Vol.23,20032.2.1(CSP),(3),.Monser[18]12,.,.(3),,.2.2.2(CE).Nishi[19](3).182262(18C6H4),20mmol/LTris2H3PO4,15,20kV,(3)(=1.33,Rs=9.09).1999,Macossay[20](MECC)(1)(3).2.31992,Smrcina[21],,CuCl2H2O22,,(3),19%95%,1%84%.Sannicolo[22]2,22(+)22102,(-20-55),,5%NH4OH,(-)2(3),65%90%,2%15%.33.1.3.1.12(3)2()(9),9LiAlH42,2221,12(10).(3)2,2221,12(10)BuLi,,BDPAD(11)Me2BDPAD(12).2,BDPAB(11)Me2BDPAB(12)[Rh(COD)Cl]2,,.2,36%95%.Rh2BINAP,,,.(Z)222(13),(R)2BDPAD95%,(R)2Me2BDPAB61%[6].93No.1:1,1222,22Pertici[23]3,10N,N,N,N222,2221,12(TMBNDA),.[Rh(COD)2(R23)]BF4,[Rh(NBD)2(R23)]BF4[Ir(COD)(R23)]BF4(Z)2(H2/3.5MPa,),,100%,9%ee.3.1.2Zhang[24]5,[Rh(COD)2(R211)]BF42(15),30min,ee90%,.3.1.3(17)LiAlH4THF.,,82%ee,,ee.(R)217a(R=H)(R)2,(R)217b(R=Me,Et,i2Bu,CH2Ph)(S)2,[25].3.1.4[9]322SchiffBPMBNDI[Ir(COD)Cl]2,10,(18),10,[Ir(COD)(BPMBNDI)]84%.,(R)2(+)22,22(1,12),(S)2(-),(S)2(-)(R)2(+).Cai[26](R)2382(R)220,(R)220RuCl2(cumene)1h,Ru221,21(18),85%,.,97%,ee10.7%.3.2,.,,,Simmons2Smith.[10]3816,1,122,5222,42.,16..(S)2322Schiff,cis2(R)2(+)222ee33.7%.2,5222,42.04Vol.23,2003Reetz[27](R)23Ph3PBr2(R)222,(R)222CuOTf,ee90%74%.3.3,.Shi[28](R)23BuLi23,Ti(OPri)424[23RCHOTi(OPri)4Et2Zn=0.211.41.8()],(80%92%)(22%46%ee)(R)21221225.3.4Shi[29](R)2326,Ag(I)24,(65%85%)ee(54%63%)(R)21224227.,.,,,,2,.3.5328,Pd,30,78%,ee92%.3Pd,[30].3.6Diels2AlderDiels2Alder.31,12(2,22)31,[31Yb(OTf)3=1.212.4()]2h,32.32,3221,3222233Diels2Alder3435.,,Diels2Alder(3.3%ee).32d14No.1:1,1222,22endo/exo(98%ee,endo/exo=93/7),Diels2Alder[31].R2(+)2(1),ee[32].3.7(S)2332,NaBH3CN,3637..3732232(38)39,39,LiAlH4,(4224222H2222)(40),ee58%[33].(R)234142,42(S)243(98%de),44,ee98%[34].22[35].1,1222,22C2,.,[3640],,.24Vol.23,2003References1Rosini,C.;Franzini,L.;Raffaelli,A.;Salvadon,P.Synthesis1992,503.2Zhang,Z.2H.;Li,T.2S.;Mo.L.2P.;Wang,J.2Y.J.HebeiUniv.(Nat.Sci.Ed.)2001,21,333(inChinese).(,,,,(),2001,21,333.)3Zhang,Z.2H.;Mo,L.2P.;Liu,S.2F.J.HebeiNormal.Univ.(Nat.Sci.Ed.)2001,25,226(inChinese).(,,,(),2001,25,226.)4Hu,Y.2P.;Suo,J.2L.Chem.Reag.1999,21,143(inChinese).(,,,1999,21,143.)5Brown,K.J.;Berry,M.S.;Murdoch,J.R.J.Org.Chem.1985,50,4345.6Miyano,S.;Nawa,M.;Mori,A.;Harukichi,H.Bull.Chem.Soc.Jpn.1984,57,2171.7Wang,Z.2C.;Huang,W.2H.;Zheng,Q.2H.;Fan,S.2Y.;Lin,D.2W.;Li,D.2H.J.ZhongshanUniv.(Nat.Sci.Ed.)1993,32,8(inChinese).(,,,,,,(),1993,32,8.)8Brown,K.J.;Berry,M.S.;Waterman,K.C.;Lingenfelter,D.;Murdoch,J.R.J.Am.Chem.Soc.1984,106,4717.9Zi,G.2P.;Yin,C.2L.ActaChim.Sinica1998,56,484(inChinese).(,,,1998,56,484.)10Chen,G.2M.;Chen,F.2H.;Zhou,C.2H.Chem.J.Chin.Univ.1995,16,216(inChinese).(,,,,1995,16,216.)11Shine,H.J.;Trisler,J.C.J.Am.Chem.Soc.1960,83,4054.12Shine,H.J.;Gruszecka,E.;Subotkowski,W.;Brownawell,M.;SanFilippo,J.,Jr.J.Am.Chem.Soc.1985,107,3218.13Smrcina,M.;Lorenc,M.;Hanus,V.;Kocovsky,P.Synlett1991,231.14Vyskocil,S.;Smrcina,M.;Lorene,M.;Hanus,V.;Polasek,M.;Kocovsky,P.Chem.Commun.1998,585.15Smrcina,M.;Vyskocil,S.;Maca,B.;Polasek,M.;Claxton,T.A.;Abbott,A.P.;Kocovsky,P.J.Org.Chem.1994,59,2156.16Song,D.2L.;Yang,G.2Z.Chem.Reag.2001,23,167(inChinese).(,,,2001,23,167.)17Tan,D.2M.;Wu,J.2A.;Wang,B.;Xu,Z.2L.Chin.J.Org.Chem.2001,21,64(inChinese).(,,,,,2001,21,64.)18Monser,L.I.;Greenway,G.M.;Ewing,D.F.Tetrahedron:Asymmetry1996,7,1189.19Nishi,H.;Nakamura,K.;Nakai,H.;Sato,T.J.Chromatogr.A1997,757,225.20Macosay,J.;Shamsi,S.A.;Warner,I.M.TetrahedronLett.1999,40,577.21Smrcina,M.;Lorene,M.