综述了无水氯化铈促进多种有机反应及其在有机合成和医药中间体合成中的应用,讨论了向格氏试剂或有机锂中添加无水氯化铈可以有效抑制羰基亲核加成副反应的发生,提高产率和选择性,通过这种方法能合成出各种三级醇,利用有机铈还能与腈反应得到叔甲胺产品.无水氯化铈还可以促进一些其他类型的反应顺利进行.
参考文献
[1] | Lai Y H .Grignard reagents from chemically activated magnesium[J].Synthesis,1981,8:585-604. |
[2] | Whitmore F C;Block L P .Grignard reactions XV steritally hindered aliphatic carbonyl compounds V enolization studies[J].Journal of the American Chemical Society,1942,64:1619-1621. |
[3] | Morrison J D;Lambert G .Mechanism of benzophenone reduction with the 2-norbomyl grignard reagent[J].Journal of Organic Chemistry,1972,37:1034-1037. |
[4] | Kohler E P;Petersen W D .The reaction between unsaturated ketones and organic magnesium compounds,the secondary products[J].Journal of the American Chemical Society,1933,55:1073-1076. |
[5] | Moeller T;Bailar J C;Emeleus H J.Pharmacological properties of cerium compounds in comprehensive inorganic chemistry[M].oxford:Eds Pergamon press,1973:1-101. |
[6] | Kagan H B;Namy J L .Lanthanides in organic synthesis[J].Tetrahedron Letters,1986,42:6573-6614. |
[7] | Xu Li;Singh S M;Librie F .Highly efficient nucleophilic addition of alkyl grignard regent to 17-ketosteroids in the presence of cerium(Ⅲ) chloride:systhesis of 17or-propyl-17β-hydroxy-4-androsten-3-one,an androgen receptor antagonist[J].Tetrahedron Letters,1994,35:1157-1160. |
[8] | Dimitrov V;Bratovanov S;Simova S et al.Cerium(Ⅲ) chloride as catalytic and stoichiometric promoter of the quantitative addition of organometallic teagents to (+)-camphor and -)-fenchone[J].Tetrahedron Letters,1994,35:6713-6716. |
[9] | Imamoto T;Kusumoto T;Tawarayama Y et al.Carbon-carbon bond forming geactions using cerium metal or organocerium (Ⅲ) reagents[J].Journal of Organic Chemistry,1984,49:3904-3912. |
[10] | Imamoto T;Takiyama N;Nakamura K et al.Reactions of carbonyl compounds with grignard reagents in the presence of cerium chloride[J].Journal of the Chemical Society,1989,111:4392-4398. |
[11] | Imamoto T;Sugiura Y;Takiyama N .Organocerium reagents nucleophilic addition to easily enolizable ketones[J].Tetrahedron Letters,1984,25:4233-4236. |
[12] | Imamoto T;Sugiura Y .Selective 1,2-addition of organocerium(Ⅲ) reagents to α,β-unsaturated carbonyl compounds[J].Journal of Organometallic Chemistry,1985,285:21-23. |
[13] | Imamoto T;Sugiura Y .Selective 1,2-addition of organocerium(Ⅲ) reagents to α,β-unsaturated carbonyl compounds[J].Journal of Physical Organic Chemistry,1989,2:93-102. |
[14] | Johnson C R;Tait B D .A cerium(Ⅲ) modification of the peterson reaction:methylenation of readily enolizable carbonyl compounds[J].Journal of Organic Chemistry,1987,52(02):281-283. |
[15] | Guo B S;Doubleday W;Cohen T .Allylcerium (Ⅲ) compounds,powerful new synthetic reagents.A new stereocontrolled approach to olefins and methylene-interrupted polyenes[J].Journal of the American Chemical Society,1987,109:4710. |
[16] | Nagasawa K;Ito K;Cohen T .A Cerium metal-mediated coumarin synthesis[J].Heterocycles,1989,28:703-706. |
[17] | Nagasawa K;Kanbara H;Matsushita K et al.A novel and efficient synthesis of 5-substituted and 5,6-disubstituted 4-methylcoumarins using organocerium (Ⅲ) reagents[J].Tetrahedron Letters,1985,26:6477. |
[18] | Corey E J;Ha D C .Total synthesis of venustatriol[J].Tetrahedron Letters,1988,29:3171. |
[19] | Ahn Y;Cohen T .Cerium(Ⅲ) chloride remarkably increases the rates of formation and yields of ketones in the reation of lithiom carboxylates with organolithiums[J].Tetrahedron Letters,1994,35:203-206. |
[20] | Natale N R;Yocklovich S G;Mallet B M .The reaction of lithio-alkyk-isoxazoles with acid chlorides in the presence of cerium trichloride.Direct preparation of β-keto-isoxazolyl compounds[J].Heterocycles,1986,24:2175-2178. |
[21] | Ahn Y;Cohen T .A general diastereoselective synthesis of spiroacetals related to those in ionophores via the reaction of lactones with cerium(Ⅲ) gamma-cerioalkoxide MAD reverses the diastereoselectivity of the addition of methylmetallics to a beta-keto ether[J].Journal of Organic Chemistry,1994,59:3142-3150. |
[22] | Mudryk B;Shook C A;Cohen T .Simple one-pot synthesis of spiroketals and oxaspirolactones by addition of gamma-and delta-cerioalkoxides to lactones and cyclic anhydrides[J].Journal of the American Chemical Society,1990,112:6389-6391. |
[23] | Kita Y;Matsuda S;Kitagaki Y et al.Chemistry of silyketene:a one-pot synthesis of a-silyl ketones[J].Synlett:Accounts and Rapid Communications In Synthetic Organic Chemistry,1991,6:401-402. |
[24] | Engelbert Ciganek;Kennett Square Pa .Process for the preparation of tertiary carbinamines[P].United state Patent:5306821,1994-4-26. |
[25] | Giganek E .Tertiary carbinamines by addition of organocerium reagents to nitriles and ketimines[J].Journal of Organic Chemistry,1992,57:4521-4527. |
[26] | Limanto J;Dorner B;Devine PN .Non-cryogenic CeCl3-promoted double additions of methyllithium and n-butyllithium to unsaturated nitriles[J].Synthesis: International Journal of Methods in Synthetic Organic Chemistry,2006(24):4143-4150. |
[27] | Reuman M;Beish S;Davis J;Batchelor MJ;Hutchings MC;Moffat DFC;Connolly PJ;Russell RK .Scalable synthesis of the VEGF-R2 kinase inhibitor JNJ-17029259 using ultrasound-mediated addition of MeLi-CeCL3 to a nitrile[J].The Journal of Organic Chemistry,2008(3):1121-1123. |
[28] | Xiao Z J;Timberlakc J W .Cerium(Ⅲ) chloride mediated nitrile aldol reaction:enhanced disteroselectivities using a chira organocerium complex[J].Tetrahedron Letters,1998,54:4211-4222. |
[29] | Lipshutz B H;Huff B;Vaccaro W .Synthesis of potential inhibitors of the glycosphingolipid biosynthesis[J].Tetrahedron Letters,1992,48:5855-5860. |
[30] | Denmark S E;Weber T;Piotrowski D W .Organocerium additions to SAMP-hydrazones:general synthesis of chiral[J].Journal of the Chemical Society,1987,109:2224-2225. |
[31] | Ender D;Klatt M;Funk R .Enantioselective synthesis of protected β-amino acetals and β-amino acids by 1,2 -addition of RM/CeCl3 to 3,3-ethylenedioxypropanal-SAMP-hydrazone[J].Synlett:Accounts and Rapid Communications In Synthetic Organic Chemistry,1993,3:226-228. |
[32] | Denmark S E;Edwards J P;Nisaise O .Organecerium additions to hydrazones:effects of reagent stoichiometry on efficiency and selectivity[J].Journal of Organic Chemistry,1993,58:569-578. |
[33] | Kato M;Mori A;Oschina H et al.Base-induced rearrangement of 1-(trimethylsilyl) allylic alcohols.Stereo-and regioselective synthesis of silyl enol ethers through lithium homoenolates[J].Journal of the Chemical Society,1984,106:1773. |
[34] | Bonini BF.;Fochi M.;Mazzanti G.;Ricci A.;Varchi G.;Comes-Franchini M. .Cerium(III) chloride-mediated vinylation of acylsilanes: A convenient new entry to silylated allylic alcohols[J].Synlett,2000(11):1688-1690. |
[35] | Imamoto T;Takiyama N;Nakamura K .Cerium chloride-promoted nucleophilic addition of grignard reagents to ketones,an efficient method for the synthesis of tertiary alcohols[J].Tetrahedron Letters,1985,26:4763-4766. |
[36] | Molander G A .Application of lanthanide reagents in organic synthesis[J].Chemical Reviews,1992,92:29-68. |
[37] | Brenner-weib G;giannis A;Sandhotf K .Model studies aimed at the synthesis of Frederieamyein A.A simple o-quinodimethane route to the spiro naphthalene portion[J].Tetrahedron Letters,1986,27:1986-1989. |
[38] | Bartoli G;Marcantoni E;petrini M.Cerium(Ⅲ) chloride mediated addition of grignard reagents to nitroalkanes:synthesis of N,N-disubstituted hydroxylamines[J].Journal of The Chemical Society,chemical Communications,1993:1373-1374. |
[39] | Awasthi S;Singhal S S .Enantioselective synthesis of tacrine-hyperzine A hybrids.Preparative chiral MPLC separation of their racemic mixtures and absolute configuration assignments by X-ray diffraction analysis[J].Tetrahedron:Asymmetry,1998,9(05):835-849. |
[40] | 张文耀;边占喜 .三氯化铈促进格氏试剂与二茂铁酮反应的研究[J].有机化学,2007,27(增刊):9. |
[41] | Imamoto T;Kusumoto T;Tawarayama Y et al.Carbon-carbon bond-forming reaetious using cerium metal or organocerium (Ⅲ) reagents[J].Journal of Organic Chemistry,1984,49:3904-3912. |
[42] | Imamoto T;Kusumoto T;Yokoyama M .A new aldol reaction via cerium enolates[J].Tetrahedron Letters,1983,24:5233-5236. |
[43] | Imamoto T .Carbonyl addition reactions promoted by cerium reagents[J].Pure and Applied Chemistry,1990,62:747-752. |
[44] | Fischer S.;Groth U.;Jeske M.;Schulz T. .Cerium(III)-catalyzed addition of diethylzinc to carbonyl compounds[J].Synlett,2002(11):1922-1924. |
[45] | Shenglof M;Gelman D;Molander C A et al.Lanthanide assisted cross-coupling of aryl bromides with triethylaluminum[J].Tetrahedron Letters,2003,44:8593. |
[46] | Johnson DC.;Widlanski TS. .Cerium(III) chloride-mediated reactions of sulfonamide dianions[J].The Journal of Organic Chemistry,2003(13):5300-5309. |
[47] | Montalban AG.;McKillop A.;Wittenberg LO. .Cerium(III) chloride mediated regioselective synthesis of cyclic alpha-chloro-alpha,beta-enones and alpha-chloro-beta-hydroxy ketones[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,1999(32):5893-5896. |
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