2,3-Wittig反应的研究进展
The Progress of [2,3]-Wittig Rearrangement
DOI: 10.12677/JOCR.2022.104014, PDF,   
作者: 陈书升*, 王欢欢, 张理明：浙江师范大学，化学与生命科学学院，浙江 金华
关键词: [2；3]-Wittig重排；重排前体；烯丙基化；[2；3]-Wittig Rearrangement； Substrates of Rearrangement； Allylation
摘要: [2,3]-Wittig重排不同于传统的[3,3]-Claisen重排，自发现起得到了合成化学家的广泛关注，并得到了充分的研究。由于其能实现化学键高效简洁的转化，且能得到具有高度衍生化的含烯丙基的产物，[2,3]-Wittig重排在全合成领域具有重要的地位。本文旨在从该反应的最初发现、重排前体的构建、不对成重排的实现等方面，全面系统的介绍有别于传统[3,3]-Claisen重排的[2,3]-Wittig重排反应。
Abstract: [2,3]-Wittig rearrangement is an attractive reaction, which is extremely different from the traditional [3,3]-claisen rearrangement, and has received extensive attention from chemists since its initial discovery. Due to its efficient and concise transformation of chemical bonds and the ability to obtain highly derivatized allyl-containing products, [2,3]-Wittig rearrangement plays an important role in total synthesis. This review attempts to provide comprehensive knowledge about [2,3]-Wittig rearrangement, including initial discovery, construction of substrates, asymmetrical rearrangements, and so on.
文章引用：陈书升, 王欢欢, 张理明. 2,3-Wittig反应的研究进展[J]. 有机化学研究, 2022, 10(4): 138-144. https://doi.org/10.12677/JOCR.2022.104014

参考文献

[1] Hoffmann, R.W. (1979) Stereochemistry of [2,3] Sigmatropic Rearrangements. Angewandte Chemie International Edition, 18, 563-572. [Google Scholar] [CrossRef] 
[2] Lansbury, P.T. and Pattison, V.A. (1962) Some Reactions of α-Metalated Ethers. The Journal of Organic Chemistry, 27, 1933-1939. [Google Scholar] [CrossRef] 
[3] Cast, J., Stevens, T.S. and Holmes, J. (1960) Molecular Rearrangement and Fission of Ethers by Alkaline Reagents. Journal of the Chemical Society, 3521-3527. [Google Scholar] [CrossRef] 
[4] Baldwin, J.E., De Bernardis, J. and Patrick, J.E. (1970) Anion Rearrangements: Duality of Mechanism in the Decomposition of Allylic Ether Anions and Synthetic Applications. Tetrahedron Letters, 11, 353-356. [Google Scholar] [CrossRef] 
[5] Denmark, S.E. and Cullen, L.R. (2015) Development of a Phase-Transfer-Catalyzed, [2,3]-Wittig Rearrangement. The Joural of Organic Chemistry, 80, 11818-11848. [Google Scholar] [CrossRef] [PubMed]
[6] Everett, R.K. and Wolfe, J.P. (2013) Synthesis of Substituted 3-Hydroxy-2-Furanone Derivatives via an Unusual Enolate Wittig Rearrangement/Alkylative Cyclization Sequence. Organic Letter, 15, 2926-2929. [Google Scholar] [CrossRef] [PubMed]
[7] McNally, A., Evans, B. and Gaunt, M.J. (2006) Organocatalytic Sigmatropic Reactions: Development of a [2,3] Wittig Rearrangement through Secondary Amine Catalysis. Angewandte Chemie International Edition, 45, 2116-2119. [Google Scholar] [CrossRef] [PubMed]
[8] Laconsay, C.J. and Tantillo, D.J. (2021) Metal Bound or Free Ylides as Reaction Intermediates in Metal-Catalyzed [2,3]-Sigmatropic Rearrangements? It Depends. ACS Catalysis, 11, 829-839. [Google Scholar] [CrossRef] 
[9] Still, W.C. and Mitra, A. (1978) A Highly Stereoselective Synthesis of Z-Trisubstituted Olefins via [2,3]-Sigmatropic Rearrangement. Preference for a Pseudoaxially Substituted Transition State. Journal of the American Chemical Society, 100, 1927-1928. [Google Scholar] [CrossRef] 
[10] Jiang, Y.L., Yu, H.X., Li, Y., Qu, P., Han, Y.X., Chen, J.H. and Yang, Z. (2020) Asymmetric Total Synthesis of Pre-Schisanartanin C. Journal of the American Chemical Society, 142, 573-580. [Google Scholar] [CrossRef] [PubMed]
[11] Peng, F. and Danishefsky, S.J. (2012) Total Synthesis of (+/-)-Maoecrystal V. Journal of the American Chemical Society, 134, 18860-18867. [Google Scholar] [CrossRef] [PubMed]
[12] Watanabe, K., Iwasaki, K., Abe, T., Inoue, M., Suzuki, T. and Katoh, T. (2005) Enantioselective Total Synthesis of (-)-Candelalide A, a Novel Blocker of the Voltage-Gated Potassium Channel Kv1.3 for an Immunosuppressive Agent. Organic Letter, 7, 3745-3748. [Google Scholar] [CrossRef] [PubMed]
[13] Durst, T., Van den Elzen, R. and LeBelle, M.J. (1972) Base-Induced Ring Enlargements of 1-Benzyl- and 1-allyl-2-azetidinones. Journal of the American Chemical Society, 94, 9261-9263. [Google Scholar] [CrossRef] 
[14] Coldham, I., Collis, A.J., Mould, R.J. and Rathmell, R.E. (1995) Ring Expansion of Aziridines to Piperidines Using the Aza-Wittig Rearrangement. Tetrahedron Letters, 36, 3557-3560. [Google Scholar] [CrossRef] 
[15] Anderson, J.C., Siddons, D.C., Smith, S.C. and Swarbrick, M.E. (1995) Aza-[2,3]-Wittig Sigmatropic Rearrangement of Crotyl Amines. Journal of the Chemical Society, Chemical Communications, 1835-1836. [Google Scholar] [CrossRef] 
[16] Anderson, J.C. and Davies, E.A. (2010) Diastereoselective Synthesis of Substituted Prolines via 5-Endo-Trig Cyclisations of Aza-[2,3]-Wittig Sigmatropic Rearrangement Products. Tetrahedron, 66, 6300-6308. [Google Scholar] [CrossRef] 
[17] Gawley, R.E. and Moon, K. (2007) Stereoselective [2,3]-Sigmatropic Rearrangements of Unstabilized Nitrogen Ylides. Organic Letter, 9, 3093-3096. [Google Scholar] [CrossRef] [PubMed]
[18] West, T.H., Daniels, D.S., Slawin, A.M. and Smith, A.D. (2014) An Isothiourea-Catalyzed Asymmetric [2,3]-Rearrangement of Allylic Ammonium Ylides. Journal of the American Chemical Society, 136, 4476-4479. [Google Scholar] [CrossRef] [PubMed]
[19] Soheili, A. and Tambar, U.K. (2011) Tandem Catalytic Allylic Amination and [2,3]-Stevens Rearrangement of Tertiary Amines. Journal of the American Chemical Society, 133, 12956-12959. [Google Scholar] [CrossRef] [PubMed]
[20] Mikami, K., Kimura, Y., Kishi, N. and Nakai, T. (1983) Acyclic Diastereoselection of the [2,3]-Wittig Sigmatropic Rearrangement of a Series of Isomeric Crotyl Ethers. A Conceptual Model for the Transition-State Geometry. The Journal of Organic Chemistry, 48, 279-281. [Google Scholar] [CrossRef] 
[21] Workman, J.A., Garrido, N.P., Sancon, J., Roberts, E., Wessel, H.P. and Sweeney, J.B. (2005) Asymmetric [2,3]- Rearrangement of Glycine-Derived Allyl Ammonium Ylids. Journal of the American Chemical Society, 127, 1066-1067. [Google Scholar] [CrossRef] [PubMed]
[22] Rodriguez, R.I., Ramirez, E., Fernandez-Salas, J.A., Sanchez-Obregon, R., Yuste, F. and Aleman, J. (2018) Asymmetric [2,3]-Wittig Rearrangement: Synthesis of Homoallylic, Allenylic, and Enynyl Alpha-Benzyl Alcohols. Organic Letter, 20, 8047-8051. [Google Scholar] [CrossRef] [PubMed]
[23] Blackburn, T.J., Kilner, M.J. and Thomas, E.J. (2015) Synthetic Approaches to Phomactins: On the Stereoselectivity of Some [2,3]-Wittig Rearrangements. Tetrahedron, 71, 7293-7309. [Google Scholar] [CrossRef] 
[24] Kawasaki, T. and Kimachi, T. (1999) Sparteine-Mediated Enantioselective [2,3]-Wittig Rearrangement of Allyl Ortho-Substituted Benzyl Ethers and Ortho-Substituted Benzyl Prenyl Ethers. Tetrahedron, 55, 6847-6862. [Google Scholar] [CrossRef] 
[25] Kennedy, C.R., Guidera, J.A. and Jacobsen, E.N. (2016) Synergistic Ion-Binding Catalysis Demonstrated via an Enantioselective, Catalytic [2,3]-Wittig Rearrangement. ACS Central Science, 2, 416-423. [Google Scholar] [CrossRef] [PubMed]
[26] Xu, X., Zhang, J., Dong, S., Lin, L., Lin, X., Liu, X. and Feng, X. (2018) Nickel(II)-Catalyzed Asymmetric Propargyl [2,3] Wittig Rearrangement of Oxindole Derivatives: A Chiral Amplification Effect. Angewandte Chemie International Edition, 57, 8734-8738. [Google Scholar] [CrossRef] [PubMed]

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