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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 2
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Original Articles

Versatile Spirocyclic Glycine‐Based Nitrones and Their Highly Stereoselective 1,3‐Dipolar Cycloaddition

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Pages 297-308 | Received 16 Mar 2006, Published online: 25 Jul 2007

References

  • Padwa , A. and Pearson , W. H. 2002 . Synthetic Applications of 1,3‐Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products Edited by: Padwa , A. and Pearson , W. H. New York : John Wiley . For reviews of nitrone cycloaddition reactions and their application in organic synthesis, see (a)
  • Gothelf , K. V. and Jørgensen , K. A. 1998 . Asymmetric 1,3‐dipolar cycloaddition reactions . Chem. Rev. , 98 : 863 – 909 .
  • Singha , K. , Roy , A. , Dutta , P. K. , Tripathi , S. , Sahabuddin , S. , Achari , B. and Mandal , S. B. 2004 . Intramolecular nitrone cycloaddition reaction on carbohydrate‐based precursors: application in the synthesis of spironucleosides and spirobisnucleosides . J. Org. Chem. , 69 : 6507 – 6510 .
  • Zanobini , A. , Gensini , M. , Magull , J. , Vidovic , D. , Kozhushkov , S. I. and Brandi , A. 2004 . A convenient new synthesis of 3‐substituted β‐lactams formally derived from 1‐(aminomethyl)‐cyclopropanecarboxylic acids . Eur. J. Org. Chem. , 20 : 4158 – 4166 .
  • Shindo , M. , Ohtsuki , K. and Shishido , K. 2005 . Asymmetric inverse electron‐demand 1,3‐dipolar cycloaddition of ynolates with a chiral nitrone derived from L‐serine leading to β‐amino acid derivatives . Tetrahedron Asymmetry , 37 : 2821 – 2831 .
  • Li , X. , Takahashi , H. , Ohtake , H. and Ikegami , S. 2004 . 1,3‐Dipolar cycloaddition of exo‐methylenesugars with nitrone: Approach to new amino‐C‐ketosyl disaccharides . Tetrahedron Lett. , 45 : 4123 – 4126 .
  • Merino , P. , Anoro , S. , Merchan , F. L. and Tejero , T. 2000 . 1,3‐Dipolar cycloaddition between hetaryl nitrones and methyl acrylates . Heterocycles , 53 : 861 – 875 .
  • Merino , P. , Anoro , S. , Franco , S. , Merchan , F. L. , Tejero , T. and Tunon , V. 2000 . 1,3‐Dipolar cycloaddition of furfurl nitrones with methyl acrylates: A convenient approach to protected 4‐hydroxypyroglutamic acids . J. Org. Chem. , 65 : 1590 – 1596 .
  • Katagiri , N. , Okada , M. , Morishita , Y. and Kaneko , C. 1997 . Syntheis of chiral spiro 3‐oxazoli‐5‐one (chiral nitrones) via a nitrosoketene intermediate and their asymmetric 1,3‐dipolar cycloaddition reactions leading to the EPC synthesis of modified amino acids . Tetrahedron , 53 : 5727 – 5746 .
  • Westermann , B. , Walter , A. , Florke , U. and Altenbach , H.‐J. 2001 . Chiral auxiliary based approach toward the synthesis of C‐glycosylated amino acids . Org. Lett. , 3 : 1375 – 1378 .
  • Baldwin , S. W. and Long , A. 2004 . 2‐tert‐Butyl‐3‐methyl‐2,3‐dihydroimidazol‐one‐N‐oxide: A new nitrone‐based chiral glycine equivalent . Org. Lett. , 6 : 1653 – 1656 .
  • Ondrus , V. , Orsag , M. , Fisera , L. and Pronayova , N. 1999 . Stereoselectivity of N‐benzyl‐C‐ethoxycarbonyl nitrone cycloaddition to (S)‐5‐hydroxymethyl‐2(5H)‐furanone and its derivates . Tetrahedron , 55 : 10425 – 10436 .
  • Dugovic , B. , Fisera , L. , Hametner , C. and Pronayova , N. 2003 . ARKIVOC , : 162 – 169 .
  • Tamura , O. , Mita , N. , Okabe , T. , Yamaguchi , T. , Fukushima , C. , Yamashita , M. , Morita , Y. , Morita , N. , Ishibashi , N. and Masanori , S. 2001 . Tandem transesterification and intramolecular cycloaddition of α‐methoxycarbonylnitrones with chiral acyclic allyl alcohols: Systematic studies on the factors affecting diastereofacial selectivity of the cycloaddition . J. Org. Chem. , 66 : 2602 – 2610 .
  • Davis , A. C. and Levy , A. L. 1951 . Interaction of α‐amino nitriles and aldehydes and ketones . J. Chem. Soc. , : 3479 – 3489 .

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