Improved Synthesis of γ-Lactones from Cyclopropyl Cyanoesters

REFERENCES

• (a) For examples, see Park , H. S. ; Kwon , D. W. ; Lee , K. ; Kim , Y. H. A novel synthesis of γ-lactones by tandem epoxide opening-cyclization reaction mediated by samarium(II) diiodide . Tetrahedron Lett. 2008 , 49 , 1616 , and references therein; (b) Purohit , V. C. ; Matla , A. S. ; Romo , D. Concise synthesis of spirocyclic, bridged γ-butyrolactones via stereospecific, dyotropic rearrangements of β-lactones involving 1,2-acyl and δ-lactone migrations . J. Am. Chem. Soc. 2008 , 130 , 10478 ; (c) Chen , M. S. ; White , M. C. A predictably selective aliphatic C–H oxidation reaction for complex molecule synthesis . Science 2007 , 318 , 783 ; (d) Fischer , D. ; Theodorakis , E. A. Studies on the synthesis of Schisandraceae natural products: Exploring a cyclopropylcarbinol ring expansion strategy . Eur. J. Org. Chem. 2007 , 4193 .
   Google Scholar
• Schwarz , J. B. ; Gibbons , S. E. ; Graham , S. R. ; Colbry , N. L. ; Guzzo , P. R. ; Le , V.-D. ; Vartanian , M. G. ; Kinsora , J. J. ; Lotarski , S. M. ; Li , Z. ; Dickerson , M. R. ; Su , T.-Z. ; Weber , M. L. ; El-Kattan , A. ; Thorpe , A. J. ; Donevan , S. D. ; Taylor , C. P. ; Wustrow , D. J. Novel cyclopropyl β-amino acid analogues of pregabalin and gabapentin that target the α 2-δ protein . J. Med. Chem. 2005 , 48 , 3026 .
   PubMed Web of Science ®Google Scholar
• (a) Babler , J. H. ; Spina , K. P. A tandem Michael reaction–cycloalkylation utilizing 2-nitropropane: A facile route to the acid component of insecticidal pyrethroids . Tetrahedron Lett. 1985 , 26 , 1923 ; (b) Ono , N. ; Tetsuya , Y. ; Isami , H. ; Kamimura , A. ; Kaji , A. Nitro compounds as nucleophilic alkylidene transfer reagents . J. Org. Chem. 1985 , 50 , 2806 ; (c) Mélot , J.-M. ; Texier-Boullet , F. ; Foucaud , A. Cyclopropanation of electrophilic alkenes with nitroalkanes in the presence of alumina-supported potassium fluoride . Synthesis 1987 , 364 .
   Google Scholar
• (a) Canonne , P. ; Bélanger , D. ; Lemay , G. ; Foscolos , G. B. One-step spiroannulation: Synthesis of spiro γ- and δ-lactones . J. Org. Chem. 1981 , 46 , 3091 ; (b) Hölemann , A. ; Reissig , H.-U. Synthesis of new furan derivatives and 4-hydroxy aldehydes from 4-hydroxy 1-enol ethers . Synthesis 2004 , 1963 .
   Google Scholar
• Kolsaker , P. ; Jensen , A. K. Protolysis of cyclopropanes with geminal electronegative substituents . Acta Chem. Scand. Ser. B42 1988 , 345 .
   Google Scholar
• (a) Bus , J. ; Steinberg , H. ; de Boer , T. J. The isomerisation and decarboxylation of cyclopropane-1,1-dicarboxylic acids . Tetrahedron Lett. 1966 , 1979 ; (b) See also: Deno , N. C. ; Billups , W. E. ; La Vietes , D. ; Scholl , P. C. ; Schneider , S. Protonated cyclopropane intermediates in the reactions of cyclopropanecarboxylic acids . J. Am. Chem. Soc. 1970 , 92 , 3700 ; (c) Rao , V. S. A convenient preparation of 2-carboxy- and 2-alkoxycarbonyl-r-butyrolactones from cyclopropane-1,1-dicarboxylic acid . Synth. Commun. 1989 , 19 , 1389 .
   Google Scholar
• (a) Krapcho type: Klemmensen , P. D. ; Kolind-Andersen , H. ; Madsen , H. B. ; Svendsen , A. Convenient synthesis of ethyl (±)-cis- and trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate . J. Org. Chem. 1979 , 44 , 416 ; (b) Yadav , V. K. ; Balamurugan , R. Silicon-assisted ring opening of donor−acceptor substituted cyclopropanes: An expedient entry to substituted dihydrofurans . Org. Lett. 2001 , 3 , 2717 ; (c) Effected with poly-4-vinyl pyridine: Solabannavar , S. B. ; Helavi , V. B. ; Desai , U. V. ; Mane , R. B. A novel short synthesis of norbisabolide . Tetrahedron Lett. 2002 , 43 , 4535 .
   Google Scholar
• Lactones bearing 5-aryl and 4-carboalkoxy substituents are available through a similar hydrolysis of Meldrum's acid–derived cyclopropane triesters, which decarboxylate under neutral or mildly basic conditions: Chen , Y. ; Ding , W. ; Cao , W. ; Lu , C. Stereoselective synthesis of trans-β-methoxycarbonyl-γ-aryl-γ-butyrolactones. Synth. Commun. 2002, 32, 1953.
   Web of Science ®Google Scholar
• Eliel , E. L. ; Hutchins , R. O. ; Knoeber , M. Diethyl tert-butylmalonate . Org. Synth. 1970 , 50 , 38 .
   Google Scholar
• Ketone example: Holmberg , C. Synthese und Eigenschaften einiger tert-Alkylmalonsäurederivate . Liebigs Ann. Chem. 1981 , 748 ; Aldehyde example: Cardillo , G. ; Gentilucci , L. ; Gianotti , M. ; Perciaccante , R. ; Tolomelli , A. Synthesis of aziridine-2,2-dicarboxylates via 1,4-addition of N,O-(bistrimethylsilyl)hydroxylamine to α, β-unsaturated malonates . J. Org. Chem. 2001 , 66 , 8657 .
   Google Scholar
• Piperidinium acetate has been shown to catalyze the Knoevenagel reaction of malonates with aldehydes, which required refluxing conditions and azeotropic H2O removal: Verhé , R. ; De Kimpe , N. ; De Buyck , L. ; Courtheyn , D. ; Schamp , N. Thermal lactonization of brominated alkylidenemalonates: Synthesis of 2-buten-4-olides . Bull. Soc. Chim. Belg. 1978 , 87 , 215 .
   Google Scholar
• Verhé , R. ; De Kimpe , N. ; De Buyck , L. ; Courtheyn , D. ; Schamp , N. Preparation of 2,2-dialkylcyclopropanes geminally substituted with electron-withdrawing groups . Synthesis 1978 , 530 .
   Google Scholar
• Alfonso , M. E. ; Hernández , M. I. ; Gómez , M. ; Jano , P. ; Pekerar , S. On the question of free radical intermediacy in cycloaddition reactions of diazocarbonyl compounds to olefins under copper(II) chelate catalysis . Tetrahedron 1985 , 41 , 2347 .
   Google Scholar