Efficient Methods for the Synthesis of Benzopyrano[3,4-c]pyrrolidines by Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with 3-Substituted Coumarins

REFERENCES

• For reviews, see (a) Pellissier , H. Asymmetric 1,3-dipolar cycloadditions . Tetrahedron 2007 , 63 , 3235 – 3285 ; (b) Gothelf , K. V. ; Jørgensen , K. A. Asymmetric 1,3-dipolar cycloaddition reactions . Chem. Rev. 1998 , 98 , 863 – 909 .
   Web of Science ®Google Scholar
• Sardina , F. J. ; Rapoport , H. Enantiospecific synthesis of heterocycles from α-amino acids . Chem. Rev. 1996 , 96 , 1825 – 1872 .
   PubMed Web of Science ®Google Scholar
• (a) Garner , P. ; Ho , W. B. ; Shin , C. The asymmetric synthesis of (−)-quinocarcin via a 1,3-dipolar cycloadditive strategy . J. Am. Chem. Soc. 1993 , 115 , 10742 – 10753 ; (b) Fiswick , C. W. G. ; Foster , R. J. ; Carr , R. E. A short dipolar cycloaddition approach to γ-lactam alkaloids from Cynometra hankei . Tetrahedron Lett. 1996 , 37 , 3915 – 3918 ; (c) Selvakumar , N. ; Azhagan , A. M. ; Srinivas , D. ; Krishna , G. G. A direct synthesis of 2-arylpropenoic acid esters having nitro groups in the aromatic ring: A short synthesis of (±)-coerulescine and (±)-horsfiline . Tetrahedron Lett. 2002 , 43 , 9175 – 9178 ; (d) Coldham , I. ; Crapnell , K. M. ; Fernandez , J. C. ; Moseley , J. D. ; Rabot , R. Synthesis of the ABC ring system of manzamine A . J. Org. Chem. 2002 , 67 , 6181 – 6187 ; (e) Pandey , G. ; Laha , J. K. ; Lakshmaiah , G. Stereoselective construction of X-azabicyclo[m.2.1]alkanes by [3 + 2]-cycloaddition of non-stabilized cyclic azomethine ylides: Synthesis of enantiopure constrained amino acids and formal total synthesis of optically active epibatidine . Tetrahedron 2002 , 58 , 3525 – 3534 ; (f) Onishi , T. ; Sebahar , P. R. ; Williams , R. M. Concise, asymmetric total synthesis of spirotryprostatin A . Tetrahedron 2004 , 60 , 9503 – 9515 ; (g) Pandey , G. ; Banerjee , P. ; Kumar , R. ; Puranik , V. G. Stereospecific route to 5,11-methanomorphanthridine alkaloids via intramolecular 1,3-dipolar cycloaddition of nonstabilized azomethine ylide: Formal total synthesis of (±)-pancracine . Org. Lett. 2005 , 7 , 3713 – 3716 ; (h) Arumugam , N. ; Jayashankaran , J. ; Manian , R. D. R. S. ; Raghunathan , R. A novel access to highly functionalised β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction . Tetrahedron 2005 , 61 , 8512 – 8516 ; (i) Hong , S. W. ; Yang , J. H. ; Weinreb , S. M. Construction of an advanced tetracyclic intermediate for total synthesis of the marine alkaloid sarain A . J. Org. Chem. 2006 , 71 , 2078 – 2089 .
   Web of Science ®Google Scholar
• Xie , J. W. ; Yoshida , K. ; Takasu , K. ; Takemoto , Y. Thiourea-catalyzed asymmetric formal [3 + 2] cycloaddition of azomethine ylides with nitroolefins. Tetrahedron Lett. 2008, 49, 6910–6913.
   Web of Science ®Google Scholar
• Horning , E. C. ; Horning , M. G. ; Dimmig , D. A. 3-Carbethoxycoumarin . Org. Synth. Coll. 1955 , 3 , 165 – 166 .
   Google Scholar
• Dauzonne , D. ; Royer , R. A convenient one-flask synthesis of 3-nitrocoumarins . Synthesis 1983 , 836 – 837 .
   Google Scholar