Efficient Synthesis of a New Type of Baylis–Hillman Adducts and Their Stereoselective Bromination

REFERENCES

• (a) Baylis , A. B. ; Hillman , M. E. D. Verfahren zur herstellung von acrylrerbindungen . German Patent 21155113 , 1972; Chem. Abstr. 1972 , 77 , 34174 ; (b) Basavaiah , D. ; Rao , A. J. Recent advances in the Baylis–Hillman reaction and applications . Chem. Rev. 2003 , 103 , 811 – 891 ; (c) Singh , V. ; Batra , S. Advances in the Baylis–Hillman reaction–assisted synthesis of cyclic frameworks . Tetrahedron 2008 , 64 , 4511 – 4574 .
   Google Scholar
• (a) Basavaiah , D. ; Roy , S. Dimethyl sulfide–induced [3 + 2] annulation strategy: An efficient synthesis of functionalized dihydropyrazole derivatives using the Baylis−Hillman bromides . Org. Lett. 2008 , 10 , 1819 – 1822 ; (b) Deng , J. ; Hu , X. ; Huang , J. ; Yu , S. ; Wang , D. ; Duan , Z. ; Zheng , Z. Enantioselective synthesis of β 2-amino acids via Rh-catalyzed asymmetric hydrogenation with BoPhoz-type ligands: Important influence of an N-H proton in the ligand on the enantioselectivity . J. Org. Chem. 2008 , 73 , 2015 – 2017 ; (c) Ye , L. ; Sun , X. ; Wang , Q. ; Tang , Y. Phosphine-catalyzed intramolecular formal [3 + 2] cycloaddition for highly diastereoselective synthesis of bicyclo[n.3.0] compounds . Angew. Chem., Int. Ed. Engl. 2007 , 46 , 5951 – 5954 ; (d) Paquette , L. A. ; Rothhaar , R. R. ; Isaac , M. ; Rogers , M. ; Rogers , R. D. Diastereo- and enantiodifferentiation in indium-promoted allylations of 2,3-azetidinediones in water: Definition of long-range stereocontrol elements on π-facial selectivity for β-lactam synthesis . J. Org. Chem. 1998 , 63 , 5463 – 5472 .
   PubMedGoogle Scholar
• (a) Lee , M. ; Lee , K. Y. ; Kim , J. N. Synthesis of N-benzyl 3,5-disubstituted piperidines via double Michael addition strategy. Bull. Korean Chem. Soc. 2005, 26, 477–480; (b) Marson , C. M. ; Pink , J. H. ; Hall , D. ; Hursthouse , M. B. ; Malik , A. ; Smith , C. An asymmetric synthesis of aza analogues of the tricyclic skeleton of daphnane and the ABC ring system of phorbol. J. Org. Chem. 2003, 68, 792–798.
   Google Scholar
• (a) Lawrence , N. J. ; Crump , J. P. ; McGown , A. T. ; Hadfield , J. A. Reaction of Baylis–Hillman products with Swern and Dess–Martin oxidants . Tetrahedron Lett. 2001 , 42 , 3939 – 3941 ; (b) McFadden , H. G. ; Harris , R. L. N. ; Jenkins , C. L. D. Potential inhibitors of phosphoenolpyruvate carboxylase, II: Phosphonic acid substrate analogs derived from reaction of trialkyl phosphites with halomethacrylates . Aust. J. Chem. 1989 , 42 , 301 – 314 ; (c) Chavan , S. P. ; Ethiraj , K. S. ; Kamat , S. K. Facile synthesis of 2Z-2-chloromethyl aryl-2-enoates . Tetrahedron Lett. 1997 , 38 , 7415 – 7416 .
   Web of Science ®Google Scholar
• (a) Liu , Y. ; Zheng , H. ; Xu , D. ; Xu , Z. ; Zhang , Y. An efficient and stereoselective synthesis of (Z)-allyl chlorides from Baylis–Hillman adducts using Vilsmeier–Haack reagent . Org. Prep. Proced. Int. 2007 , 39 , 190 – 194 ; (b) Lee , C. H. ; Jung , H. J. ; Kim , J. H. ; Jeong , W. J. ; Cho , J. M. ; Ro , S. ; Hyun , Y. L. ; Shin , D. ; Lee , C. S. Preparation of alkylcarbamoyl naphthalenyloxyoctenoyl hydroxyamides as histone deacetylase (HDAC) inhibitors . WO Patent 2007052938, 2007 ; Chem. Abstr. 2007 , 146 , 500748 ; (c) Saxena , R. ; Singh , V. ; Batra , S. Studies on the catalytic hydrogenation of Baylis–Hillman derivatives of substituted isoxazolecarbaldehydes: Unusual retention of isoxazole ring during Pd–C–promoted hydrogenation of Baylis–Hillman adducts . Tetrahedron 2004 , 60 , 10311 – 10320 .
   Web of Science ®Google Scholar
• (a) Ye , L. ; Han , X. ; Sun , X. ; Tang , Y. PPh3-catalyzed ylide cyclization for the controllable synthesis of benzobicyclo[4.3.0] compounds: Base effects and scope . Tetrahedron 2008 , 64 , 1487 – 1493 ; (b) Mitra , S. ; Gurrala , S. R. ; Coleman , R. S. Total synthesis of the eupomatilones . J. Org. Chem. 2007 , 72 , 8724 – 8736 ; (c) Das , B. ; Venkateswarlu , K. ; Krishnaiah , M. ; Holla , H. ; Majhi , A. A rapid and efficient stereoselective synthesis of (Z)- and (E)-allyl bromides from Baylis–Hillman adducts using bromo(dimethyl)sulfonium bromide . Helv. Chim. Acta 2006 , 89 , 1417 – 1421 ; (d) Das , B. ; Majhi , A. ; Banerjee , J. ; Chowdhury , N. ; Venkateswarlu , K. A highly efficient stereoselective synthesis of (Z)- and (E)-allyl iodides from Baylis–Hillman adducts . Tetrahedron Lett. 2005 , 46 , 7913 – 7915 ; (e) Das , B. ; Holla , H. ; Srinivas , Y. ; Chowdhury , N. ; Bandgar , B. P. Studies on novel synthetic methodologies, part 137: An expedient stereoselective synthesis of (Z)- and (E)-allyl iodides from Baylis–Hillman adducts along with selective iodination of benzylic alcohols using the polymethylhydrosiloxane–iodine system . Tetrahedron Lett. 2007 , 48 , 3201 – 3204 ; (f) Das , B. ; Kanth , B. S. ; Reddy , K. R. ; Satyalakshmi , G. ; Kumar , R. A. A simple and efficient protocol for chlorination of Baylis–Hillman adducts using PPh3/CCl4 . Chem. Lett. 2008 , 37 , 512 – 513 ; (g) Das , B. ; Chowdhury , N. ; Damodar , K. ; Ravikanth , B. A mild and efficient method for chlorination of Baylis–Hillman adducts using PPh3/Cl3CCONH2 . Helv. Chim. Acta 2007 , 90 , 2037 – 2040 .
   Google Scholar
• (a) Sa , M. M. ; Ramos , M. D. ; Fernandes , L. Fast and efficient preparation of Baylis–Hillman–derived (E)-allylic azides and related compounds in aqueous medium. Tetrahedron 2006, 62, 11652–11656; (b) Ying , T. ; Bao , W. ; Wang , Z. ; Zhang , Y. Highly efficient and stereoselective synthesis of (2Z)-2-(halomethyl)alk-2-enoates in acidic ionic liquid. J. Chem. Res. 2005, 2, 96–98; (c) Li , J. ; Wang , X. ; Zhang , Y. Direct and highly efficient synthesis of (Z)-allyl iodides from Baylis–Hillman adducts promoted by TMSCl/NaI system. Synlett 2005, 1039–1041; (d) Das , B. ; Banerjee , J. ; Ravindranath , N. ; Venkataiah , B. Convenient and efficient stereoselective synthesis of (2Z)-2-(chloromethyl)alk-2-enoates using iron(III) or indium(III) chloride. Tetrahedron Lett. 2004, 45, 2425–2426; (e) Das , B. ; Banerjee , J. ; Ravindranath , N. A simple and facile stereoselective synthesis of (Z)- and (E)-allyl halides catalyzed by silica supported sodium hydrogen sulfate: Factors influencing the yields and stereochemistry of allyl halides. Tetrahedron 2004, 60, 8357–8361; (f) Ravichandran , S. Facile stereoselective synthesis of (E)- and (Z)-allyl bromides from the Baylis–Hillman adducts using MgBr2 . Synth. Commun. 2001, 31, 2059–2062; (g) Gruiec , A. ; Foucaud , A. ; Moinet , C. Reactivity of silica gel–supported copper(II) bromide: Regioselective synthesis of allylic bromides. New J. Chem. 1991, 15, 943–947.
   Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Madan , C. Montmorillonite clay–catalyzed stereoselective syntheses of aryl-substituted (E)- and (Z)-allyl iodides and bromides . New J. Chem. 2001 , 25 , 1114 – 1117 .
   Google Scholar
• Su , W. ; Zhuang , Y. ; Wu , D. ; Zhong , W. A convenient synthesis of β-chlorovinylaldehydes with bis-(trichloromethyl) carbonate . Org. Prep. Proced. Int. 2007 , 39 , 195 – 199 .
   Web of Science ®Google Scholar
• (a) Zhong , W. ; Lin , F. ; Chen , R. ; Su , W. An efficient synthesis of 2-hydroxy-7,8-dihydroquinolin-5(6H)-ones and 7,8-dihydroquinoline-2,5(1H,6H)-diones from Morita–Baylis–Hillman adduct acetates . Synthesis 2008 , 2561 – 2568 ; (b) Zhong , W. ; Zhao , Y. ; Guo , B. ; Wu , P. ; Su , W. Dramatically accelerated addition under solvent-free conditions: An efficient synthesis of (E)-1,2,4-triazole-substituted alkenes from Baylis–Hillman acetates . Synth. Commun. 2008 , 38 , 3291 – 3302 ; (c) Zhong , W. ; Zhao , Y. ; Su , W. An efficient synthesis of 3-arylmethyl-7,8-dihydro-6H-chromene-2,5-diones from Baylis–Hillman adduct acetates under solvent-free conditions . Tetrahedron 2008 , 64 , 5491 – 5496 .
   Google Scholar
• Romagnoli , R. ; Baraldi , P. G. ; Carrion , M. D. ; Cara , C. L. ; Cruz-Lopez , O. ; Preti , D. ; Tolomeo , M. ; Grimaudo , S. ; Di Cristina , A. ; Zonta , N. ; Balzarini , J. ; Brancale , A. ; Sarkar , T. ; Hamel , E. Design, synthesis, and biological evaluation of thiophene analogues of chalcones . Bioorg. Med. Chem. 2008 , 16 , 5367 – 5376 .
   PubMed Web of Science ®Google Scholar
• Rappoport , Z. ; Gazit , A. Nucleophilic attacks on carbon–carbon double bonds, 33: Approaching the retention region from the stereoconvergence region in nucleophilic substitution of (E)- and (Z)-methyl p-substituted-α-formyl- and α-(tert-butoxycarbonyl)-β-halocinnamates . J. Org. Chem. 1986 , 51 , 4112 – 4131 .
   Google Scholar