Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 17
228
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Simple and Advantageneous Stereoselective Synthesis of (Z)-Allyl Phosphonates Starting from Baylis–Hillman Adducts

, &
Pages 2479-2489 | Received 01 Dec 2010, Published online: 29 May 2012

REFERENCES

  • (a) Baylis , A. B. ; Hillman , M. E. D. German Patent 2155113, 1972 ; Chem. Abstr. 1972 , 77 , 341749 ; (b) Basavaiah , D. ; Rao , A. J. ; Satayanarayana , T. Recent advances in the Baylis–Hillman reaction and applications . Chem. Rev. 2003 , 103 , 811 ; (c) Basavaiah , D. ; Reddy , B. S. ; Badsara , S. S. Recent contributions from the Baylis–Hillman reaction to organic chemistry . Chem. Rev. 2010 , 110 , 5447 .
  • (a) Hoffmann , H. M. R. ; Rabe , J. Synthesis and biological activity of α-methylene-γ-butyrolactones. Angew. Chem. Int. Ed. 1985, 24, 94; (b) Buchholz , R. ; Hoffman , H. M. R. α -methylidene- and α-alkylidene-β-lactams from nonproteinogenic amino acids. Helv. Chem. Acta 1991, 74, 1213; (c) Basavaiah , D. ; Sarma , P. K. S. ; Bhavani , A. K. D. Applications of Baylis–Hillman coupling products: A remarkable reversal of stereochemistry from esters to nitriles: A simple synthesis of (2E)-2-methylalk-2-en-1-ols and (2Z)-2-methylalk-2-enenitriles. Chem. Commun. 1992, 955; (d) Basavaiah , D. ; Sarma , P. K. S. ; Bhavani , A. K. D. Applications of the Baylis–Hillman reaction: A simple stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes. Chem. Commun. 1994, 1091; (e) Basavaiah , D. ; Bakthadoss , M. ; Pandiaraju , S. A new protocol for the syntheses of (E)-3-benzylidenechroman-4-ones: A simple synthesis of the methyl ether of bonducellin S. Chem. Commun. 1998, 1639; (f) Das , B. ; Banerjee , J. ; Mahender , G. ; Majhi , A. Organic reactions in water: An efficient zinc-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes using unactivated alkyl halides. Org. Lett. 2004, 6, 3349; (g) Das , B. ; Damodar , K. ; Bhunia , N. ; Shashikanth , B. Mild and practical stereoselective synthesis of (Z)- and (E)-allyl bromides from Baylis–Hillman adducts using Appel agents (PPh3/CBr4): A facile synthesis of semiplenamides C and E. Tetrahedron Lett. 2009, 50, 2072; (h) Singh , V. ; Batra , S. Advances in the Baylis–Hillman reaction–assisted synthesis of cyclic frameworks. Tetrahedron 2008, 64, 4511, and references cited therein.
  • (a) Janeski , T. ; Bodalski , R. A convenient method for the synthesis of substituted 2-methoxycarbonyl- and 2-cyano-allylphosphonates: The allyl phosphite–allylphosphonate rearrangement . Synthesis 1990 , 799 ; (b) Basavaiah , D. ; Pandiaraju , S. Nucleophilic addition of triethyl phosphite to acetates of the Baylis–Hillman adducts: Stereoselective synthesis of (E)- and (Z)-allylphosphonates . Tetrahedron 1996 , 52 , 2261 .
  • (a) Kerst , A. F. ; Douros Jr. , J. D. Diethyl allyl phosphonates as an antimicrobial agent. U.S. Patent 3783160, 1974 ; (b) Ettari , R. ; Nizi , E. ; Di Francesco , M. E. ; Micale , N. ; Grasso , S. ; Zappala , M. ; Vicik , R. ; Schirmeister , T. Nonpeptidic vinyl and allyl phosphonates as falcipain-2 inhibitors . Chem. Med. Chem. 2008 , 3 , 1030 .
  • (a) Janeski , T. ; Bodalski , R. A convenient Horner–Emmons approach to the synthesis of substituted ethyl 1,3-butadiene-2-carboxylates and related compounds . Synthesis 1989 , 506 ; (b) Attolinis , M. ; Peiffer , G. ; Maffei , M. Palladium-catalyzed acetoxylation of cyclic allyl phosphonates in the presence of isopentyl nitrite and using molecular oxygen as final oxidant . Tetrahedron 2000 , 56 , 2693 ; (c) Chemler , S. R. ; Coffey , D. S. ; Roush , W. R. An improved synthesis of the (E,Z)-dienoate precursor of (+)-damavaricin D via a vinylogous Horner–Wadsworth–Emmons reaction . Tetrahedron Lett. 1999 , 40 , 1269 ; (d) Balczewski , P. ; Bodzioch , A. Phosphorous, Sulfur Silicon Relat. Elem. 2009 , 184 , 1076 ; (e) Jang , W. B ; Lee , C.-W. ; Lee , K. ; Sung , J. W. ; Oh , D. Synthesis of 3-akyl-3-phosphoryl chromanones: Tandem allyl-vinyl migration and cyclization of α-(o-hydroxybenzoyl)-allylic phosphonates . Synth. Commun. 2001 , 31 , 2613 ; (f) Roy , V. ; Kumamoto , H. ; Nolan , S. P. ; Topalis , D. ; Deville-Bonne , D. ; Balzarini , J. ; Neyts , J. ; Andrei , G. ; Snoeck , R. ; Agrofoglio , L. A. Cross-metathesis-mediated synthesis of new acyclic nucleoside phosphonates . Nucleosides, Nucleotides 2007 , 26 , 1399 ; (g) Shen , Y. ; Ni , J. A novel sequential transformations of phosphonate: Highly stereoselective synthesis of perfluoroalkylated α-fluoro-α,β-unsaturated esters . J. Org. Chem. 1997 , 62 , 7260 .
  • (a) Das , B. ; Banerjee , J. ; Ravindranath , N. ; Venkateswarlu , K. Convenient and efficient stereoselective synthesis of (2Z)-2-(chloromethyl)alk-2-enoates using iron(III) or indium(III) chloride . Tetrahedron Lett. 2004 , 45 , 2425 ; (b) Das , B. ; Majhi , A. ; Banerjee , J. ; Chowdhary , N. ; Venkateswarlu , K. A highly efficient stereoselective synthesis of (Z)- and (E)-allyl iodides from Baylis–Hillman adducts . Tetrahedron Lett. 2005 , 46 , 7913 ; (c) Das , B. ; Chowdhary , N. ; Banerjee , J. ; Majhi , A. ; Mahender , G. A facile Zn-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from Baylis–Hillman adducts in water and its application . Chem. Lett. 2006 , 35 , 358 ; (d) Das , B. ; Majhi , A. ; Reddy , K. R. ; Venkateswarlu , K. I2–SiO2: An efficient heterogeneous catalyst for the Johnson–Claisen rearrangement of Baylis–Hillman adducts . J. Mol. Catal. A: Chem. 2007 , 263 , 273 ; (e) Das , B. ; Damodar , K. ; Chowdhary , N. ; Saritha , D. ; Ravikanth , B. ; Krishnaiah , M. α-Amido sulfones: Novel substrates for the practical and efficient aza-Morita–Baylis–Hillman reaction under neat conditions . Tetrahedron 2008 , 64 , 9396 .
  • Part 204 in the series, “Studies on novel synthetic methodologies.”

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.