Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 11
495
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Solid/Liquid Phase-Transfer Catalytic Diazo Transfer Synthesis

, , , &
Pages 1574-1579 | Received 28 Apr 2009, Published online: 06 May 2010

REFERENCES

  • (a) Callant , P. ; D'Haenens , L. ; Vandewalle , M. An efficient preparation and the intramolecular cyclopropanation of α-diazo-β-ketophosphonates and α-diazophosphonoacetates . Synth. Commun. 1984 , 14 ( 2 ), 155 – 161 ; (b) Davies , H. M. ; McAfee , M. J. ; Oldenburg , C. E. M. Scope and stereochemistry of the tandem intramolecular cyclopropanation/Cope rearrangement sequence . J. Org. Chem. 1989 , 54 ( 4 ), 930 – 936 ; (c) Davies , H. M. ; Antoulinakis , E. G. ; Hansen , T. Catalytic asymmetric synthesis of syn-aldol products from intermolecular C-H insertions between allyl silyl ethers and methyl aryldiazoacetates . Org. Lett. 1999 , 1 ( 3 ), 383 – 385 ; (d) Padwa , A. ; Sheehan , S. M. ; Straub , C. S. An isomünchnone-based method for the synthesis of highly substituted 2(1H)-pyridones . J. Org. Chem. 1999 , 64 ( 23 ), 8648 – 8659 ; (e) Davies , H. M. ; Beckwith , E. J. Catalytic enantioselective C-H activation by means of metal-carbenolid-induced C-H insertion . Chem. Rev. 2003 , 103 ( 8 ), 2861 – 2903 ; (f) Müller , P. ; Allenbach , Y. F. ; Chappellet , S. ; Ghanem , A. Asymmetric cyclopropanation and cycloaddition of dioxocarbenes . Synthesis 2006 , ( 10 ), 1689 – 1696 ; (g) Fenlon , T. W. ; Schwaebisch , D. ; Mayweg , V. W. ; Lee , V. ; Adlington , R. M. Studies towards the synthesis of lindenene: Unexpected stereochemical outcome of an intramolecular cyclopropanation reaction and synthesis of (±)-epi-lindenene and (±)-iso-lindenene . Synlett 2007 , ( 17 ), 2679 – 2682 .
  • (a) Regicz , M. Transfer of diazo groups . Angew. Chem., Int. Ed. Engl. 1967 , 6 , 733 – 743 ; (b) Hendrickson , J. B. ; Wolf , W. A. The direct introduction of the diazo function in organic synthesis . J. Org. Chem. 1968 , 33 ( 9 ), 3610 – 3618 ; (c) Regicz, M.; Maas, G. Diazo Compounds: Properties and Synthesis; Academic Press: Orlando, 1986.
  • Regitz , M. ; Anschütz , W. ; Liedhegener , A. Synthese von α-Diazo-phosphonsäureestern . Chem. Ber. 1968 , 101 , 3734 – 3743 .
  • Goddard-Borger , E. D. ; Stick , R. V. An efficient, inexpensive, and shelf-stable diazotransfer reagent: Imidazole-1-sulfonyl azide hydrochloride . Org. Lett. 2007 , 9 ( 19 ), 3797 – 3800 .
  • Khare , A. B. ; McKenna , C. E. An improved synthesis of tetraalkyl diazomthylenediphosphonates and alkyl diazo(dialkoxyphosphoryl)acetates . Synthesis 1991 , 405 – 406 .
  • (a) Taber , D. F. ; Ruckle , R. E. Jr. ; Hennessy , M. J. Mesyl azide: A superior reagent for diazo transfer . J. Org. Chem. 1986 , 51 ( 21 ), 4077 – 4078 ; (b) Baum , J. S. ; Shook , D. Diazotransfer reactions with p-acetamidobenzenesulfonyl azide . Synth. Commun. 1987 , 17 ( 14 ), 1709 – 1716 ; (c) Wurz , R. P. ; Lin , W. ; Charette , A. B. Trifluoromethanesulfonyl azide: An efficient reagent for the preparation of α-cyano-α-diazo carbonyls and an α-sulfonyl-α-diazo carbonyl . Tetrahedron Lett. 2003 , 44 ( 49 ), 8845 – 8848 ; (d) Rianelli , R. S. ; deSouza , M. C. B. V. ; Ferreira , V. F. Mild diazo transfer reaction catalyzed by modified clays . Synth. Commun. 2004 , 34 ( 5 ), 951 – 959 .
  • Green , G. M. ; Peet , N. P. ; Metz , W. A. Polystyrene supported benzenesulfonyl azide: A diazo transfer reagent that is both efficient and safe. J. Org. Chem. 2001, 66(7), 2509–2511.
  • Harned , A. M. ; Sherrill , W. M. ; Flynn , D. L. ; Hanson , P. R. High-load, soluble oligomeric benzenesulfonyl azide: Application to facile diazo-transfer reactions . Tetrahedron 2005 , 61 ( 51 ), 12093 – 12099 .
  • Shiraki , C. ; Saito , H. ; Takahashi , K. ; Urakawa , C. ; Hirata , T. Preparation of amino(diethoxyphosphoryl) acetic esters: Catalytic hydrogenation of diazo compounds to amines . Synthesis 1988 , 399 – 401 .
  • Alloum , A. B. ; Villemin , D. Potassium fluoride on alumina: An easy preparation of diazocarbonyl compounds . Synth. Commun. 1989 , 19 , 2567 – 2571 .
  • Ramachary , D. B. ; Narayana , V. V. ; Ramakumar , K. Direct ionic liquid–promoted organocatalyzed diazo-transfer reactions, diversity-oriented synthesis of diazo-compounds . Tetrahedron Lett. 2008 , 49 , 2704 – 2709 .
  • Ghosh , S. ; Datta , I. Diazo transfer reaction in solid state . Synth. Commun. 1991 , 21 ( 2 ), 191 – 200 .
  • Ledon , H. An improved preparation of α-diazocarbonyl compounds . Synthesis 1974 , 347 – 348 .
  • Tőke , L. ; Jászay , M. Z. ; Petneházy , I. ; Clementis , G. ; Vereczkey , D. G. ; Kövesdi , I. ; Rockenbauer , A. ; Kováts , K. A versatile building block for the synthesis of substituted cyclopropanephosphonic acid esters . Tetrahedron 1995 , 51 ( 33 ), 9167 – 9178 .
  • Evans , D. A. ; Britton , T. C. ; Ellman , J. A. ; Dorow , R. L. The asymmetric synthesis of α-amino acids: Electrophilic azidation of chiral imide enolates, a practical approach to the synthesis of (R)-, and (S)-α-azido carboxylic acids . J. Am. Chem. Soc. 1990 , 112 ( 10 ), 4011 – 4030 .

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.