Learn about our remote access options. Number of times cited according to CrossRef: Diastereoselective sulfur ylide rearrangements from gold catalysed oxidation of ynamides. 0000000974 00000 n L. Claisen, Chem. The reaction proceeds through a tandem Claisen rearrangement and 6‐endo‐trig or 6‐endo‐dig cyclization sequence. Development of a New Lewis Acid-Catalyzed Claisen Rearrangement Tehshik P. Yoon, Vy M. Dong, and David W. C. MacMillan* Department of Chemistry, UniVersity of California, Berkeley, California 94720 ReceiVed June 14, 1999 Since its discovery in 1912,1 the Claisen rearrangement has become one of the most powerful tools for carbon-carbon bond Manganese(I)-Catalyzed Direct C–H Allylation of Arenes with Allenes. 0000002847 00000 n Learn more. The first example of abnormal Claisen rearrangements was reported by Lauer and Filbert in 1936. The combined organic layers were dried over anhydrous MgSO4 and concentrated. Enantioselective Acyl-Claisen Rearrangement with Representative Allyl Morpholines a NR A one‐pot procedure is reported for the generation and Claisen rearrangement of benzyl vinyl ethers that contain an activating α‐alkoxy substituent on the vinyl group. Table 3. trapping of Any queries (other than missing content) should be directed to the corresponding author for the article. In general, this type of abnormal Claisen rearrangement does not occur smoothly, except when in the presence of Lewis acids FeCl3, even though other Lewis acids (e.g., HfCl4, GaCl3, ZrCl4 have limited ability to accelerate such reaction. The dark, granular residue was dissolved in EtOAc and adsorbed on 10 silica. A [3,3]‐sigmatropic mechanism was supported by trapping of the intermediate isotoluene in an intramolecular Alder–ene reaction. http://pubs.acs.org/page/copyright/permissions.html, https://doi.org/10.1021/acs.orglett.0c01012, https://doi.org/10.1021/acs.orglett.9b01619, https://doi.org/10.1021/acs.orglett.7b02644, https://doi.org/10.1021/acs.orglett.5b02843, https://doi.org/10.1002/9780470682531.pat0858, https://doi.org/10.1016/j.tet.2017.03.004, https://doi.org/10.1007/978-3-319-45934-9_4, https://doi.org/10.1016/j.tet.2016.06.049, https://doi.org/10.1016/j.molliq.2014.12.019, https://doi.org/10.1016/B978-0-08-097742-3.00624-8, https://doi.org/10.1016/j.tetlet.2012.06.088, https://doi.org/10.1016/j.comptc.2011.11.025, https://doi.org/10.1016/j.tet.2011.03.011, https://doi.org/10.1002/9780470638859.conrr068, https://doi.org/10.1016/j.tet.2010.05.045, https://doi.org/10.1002/047084289X.rk000.pub2, https://doi.org/10.1016/j.saa.2007.10.015, https://doi.org/10.1002/9780471476665.ch16, https://doi.org/10.1016/j.tet.2007.10.079, https://doi.org/10.1016/j.tetlet.2007.05.133, https://doi.org/10.1016/j.tetlet.2005.02.132, https://doi.org/10.1016/B0-08-044655-8/00009-X, https://doi.org/10.1016/B0-08-044655-8/00018-0, https://doi.org/10.1016/j.molcata.2004.09.012, https://doi.org/10.1016/j.tetlet.2004.03.089, https://doi.org/10.1016/S0040-4020(03)00491-5, https://doi.org/10.1016/S0040-4020(02)00164-3, https://doi.org/10.1002/1521-3757(20011217)113:24<4725::AID-ANGE4725>3.0.CO;2-L, https://doi.org/10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO;2-V, https://doi.org/10.1016/S0040-4020(01)00349-0. R1 R2 OH R1 R2 O R3 X R1 R2 O R3 X R1 O X R2 R3 [3,3] 1. A one‐pot procedure is reported for the generation and Claisen rearrangement of benzyl vinyl ethers that contain an activating α‐alkoxy substituent on the vinyl group. 0000004580 00000 n To a solution of BINOL (0.22 mmol) in 4 mL distilled CH2Cl2 was added 200 μL 1.0 M SnCl4 in CH2Cl2 (0.2 mmol) at −78°C under argon atmosphere. 59 0 obj<>stream Claisen rearrangements of benzyl vinyl ethers are much less facile than those of aliphatic allyl vinyl ethers, and their synthetic utility has remained relatively unexplored. (4) However, much experimental evidence is inconsistent with the stepwise mechanism. Use the link below to share a full-text version of this article with your friends and colleagues.