(E)-2-Oxo-1-sulfonyl-3-alkenes as Reactive Hetero 1,3-Dienes. Absolutely endo-Selective Hetero Diels-Alder Reactions with Vinyl Ethers in the Presence of a Lewis Acid Catalyst
作者： Eiji Wada , Hiroshi Yasuoka , Shuji Kanemasa
DOI: 10.1246/CL.1994.145
关键词:
摘要: (E)-2-Oxo-1-sulfonyl-3-alkenes as new hetero 1,3-dienes undergo smooth Diels-Alder reactions with vinyl ethers in the presence of Eu(fod)3 or TiCl2(i-PrO)2. The are absolutely endo-selective producing 2,4-cis-3,4-dihydro-2H-pyrans excellent yields, sufficient catalytic cycles being attained. sulfonyl-stabilized carbanions derived from cycloadducts alkylated followed by reductive desulfonylation.
csj.jp参考文章(21)
Zeinhom M. Ismail, H. M. R. Hoffmann, New Dihydropyrans: Lewis Acid Catalyzed Cycloadditions of α,β‐Unsaturated Acyl Cyanides to Simple Unactivated Olefins and Dienes. Practical Route to Derivatives of Rose Oxide Angewandte Chemie. ,vol. 21, pp. 1819- 1825 ,(1982) , 10.1002/ANIE.198218190
Richard R Schmidt, Martin Maier, Diastereospecific synthesis of 2.6-dideoxy- and 2.4.6-trideoxy-sugars via hetero-diels-alder-reaction Tetrahedron Letters. ,vol. 26, pp. 2065- 2068 ,(1985) , 10.1016/S0040-4039(00)94780-4
Akira Sera, Meguru Ohara, Hiroaki Yamada, Emiko Egashira, Naohiro Ueda, Jun-ichiro Setsune, Tin(IV) Chloride Catalyzed Addition of Methyl 2-Oxo-3-alkenoates to Simple Alkenes Chemistry Letters. ,vol. 19, pp. 2043- 2046 ,(1990) , 10.1246/CL.1990.2043
Robert A. John, Vincent Schmid, Hugo Wyler, Facile Hetero-Diels-Alder Reaction of ?,?-Unsaturated Acyl Cyanides and Enol Ethers: Syntheses of 2-Alkoxy-3,4-dihydro-2H-Pyran-6-carbonitriles Helvetica Chimica Acta. ,vol. 70, pp. 600- 606 ,(1987) , 10.1002/HLCA.19870700313
Steven V. Ley, Barry Lygo, Francine Sternfeld, Anne Wonnacott, Alkylation reactions of anions derived from 2-benzenesulphonyl tetrahydropyran and their application to spiroketal syntiesis Tetrahedron. ,vol. 42, pp. 4333- 4342 ,(1986) , 10.1016/S0040-4020(01)87660-2
Lutz F. Tietze, Thomas. Huebsch, Edgar. Voss, Michael. Buback, Winfried. Tost, Intra- and intermolecular hetero-Diels-Alder reactions. 23. Intermolecular hetero-Diels-Alder reactions of enamino ketones at high pressure. The first significant pressure-induced diastereoselectivity in organic transformations Journal of the American Chemical Society. ,vol. 110, pp. 4065- 4066 ,(1988) , 10.1021/JA00220A071
J. L. Belletire, E. G. Spletzer, Oxidative Coupling. V. Carbon-Carbon Bond Formation From β-Ketosulfone Dianions Synthetic Communications. ,vol. 17, pp. 1701- 1707 ,(1987) , 10.1080/00397918708063987
G. Desimoni, G. Tacconi, Heterodiene syntheses with .alpha.,.beta.-unsaturated carbonyl compounds Chemical Reviews. ,vol. 75, pp. 651- 692 ,(1975) , 10.1021/CR60298A001
Masashige Yamauchi, Sadamu Katayama, Osamu Baba, Toshio Watanabe, Hetero-Diels–Alder reactions of 2-methylene-1,3-dicarbonyl compounds with alkyl vinyl ethers Journal of The Chemical Society, Chemical Communications. pp. 281- 282 ,(1983) , 10.1039/C39830000281
Samuel Danishefsky, Mark Bednarski, Lanthanide catalysis of cycloadditions of heterodienes with enol ethers Tetrahedron Letters. ,vol. 25, pp. 721- 724 ,(1984) , 10.1016/S0040-4039(01)80009-5