An Efficient Procedure for Preparation of C‐ and N‐Protected 1‐Aminocyclobutane Carboxylic Acid

References

• Allan , R. D. , Hanrahan , J. R. , Hambley , T. W. , Johnston , G. A.R. , Mewett , K. N. and Mitrovic , A. D. 1990 . Synthesis and activity of a potent N‐methyl‐D‐aspartic acid agonist, trans‐1‐aminocyclobutane‐1,3‐dicarboxylic acid, and related phosphonic and carboxylic acids . J. Med. Chem. , 33 : 2905 [PUBMED] [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Gaoni , Y. , Chapman , A. G. , Parvez , N. , Pook , P. C.‐K. , Jane , D. E. and Watkins , J. C. 1994 . Synthesis, NMDA receptor antagonist activity, and anticonvulsant action of 1‐aminocyclobutanecarboxylic acid derivatives . J. Med. Chem. , 37 : 4288 [PUBMED] [INFOTRIEVE] [CSA]
   PubMedGoogle Scholar
• Hanrahan , J. R. , Taylor , P. C. and Errington , W. 1997 . The synthesis of 3‐phosphonocyclobutyl amino acid analogues of glutamic acid via diethyl 3‐oxycyclobutylphosphonate, a versatile synthetic intermediate . J. Chem. Soc. Perkin Trans. 1 , : 493 [CROSSREF]
   Google Scholar
• Gershonov , E. , Granoth , R. , Tzehoval , E. , Gaoni , Y. and Fridkin , M. 1996 . 1‐Aminocyclobutanecarboxylic acid derivatives as novel structural elements in bioactive peptides: application to tuftsin analogs . J. Med. Chem. , 39 : 4833 [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Tsang , J. W. , Schmied , B. , Nyfeler , R. and Goodman , M. 1984 . Peptide sweeteners. 6. Structural studies on the C‐terminal amino acid of L‐aspartyl dipeptide sweeteners . J. Med. Chem. , 27 : 1663 [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Gatos , M. , Formaggio , F. , Crisma , M. , Toniolo , C. , Bonora , G. M. , Benedetti , Z. , Di Blasio , B. , Iacovino , R. , Santini , A. , Saviano , M. and Kamphuis , J. 1997 . Conformational characterization of the 1‐aminocyclobutane‐1‐carboxylic acid residue in model peptides . J. Pept. Sci. , 3 : 110 [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
   PubMedGoogle Scholar
• Srivastava , R. R. , Singhaus , R. R. and Kabalka , G. W. 1997 . 1‐Amino‐3‐[2‐(1,7‐dicarba‐closo‐dodecaboran(12)‐1‐yl)ethyl]cyclobutanecarboxylic acid: a potential BNCT agent . J. Org. Chem. , 62 : 4476 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Kalvin , D. , Ramalingam , K. and Woodard , R. 1985 . A facile procedure for the preparation of alicyclic α‐amino acids . Synth. Commun. , 15 : 267
   Google Scholar
• Park , K.‐H. and Kurth , M. J. 2000 . Diastereoselective synthesis of hydantoin‐ and isoxazoline‐substituted dispirocyclobutanoids . J. Org. Chem. , 65 : 3520 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Gaoni , Y. 1995 . Synthesis of aminocyclobutane mono‐ and dicarboxylic acids and derivatives thereof from (phenylsulfonyl)bicyclobutanes . Org. Prep. Proced. Int. , 27 : 185
   Web of Science ®Google Scholar
• Corey , E. J. , Lee , D.‐H. and Choi , S. 1992 . An enantioselective synthesis of (2S,3S)‐ and (2R,3S)‐3‐hydroxyleucine . Tetrahedron Lett. , 33 : 6735 [CROSSREF]
   Google Scholar
• Righi , G. , Rumboldt , G. and Bonini , C. 1995 . A simple route to syn α‐amino‐β‐hydroxy esters by C‐2 regioselective opening of α,β‐epoxy esters with metal halides . Tetrahedron , 51 : 13401 [CROSSREF]
   Google Scholar
• Saito , S. , Yokoyama , H. , Ishikawa , T. , Niwa , N. and Moriwake , T. 1991 . Hydrogen azide‐amine systems as an azide nucleophile for substitutions of sulfonates, halides, and vicinal disulfonates . Tetrahedron Lett. , 32 : 663 [CROSSREF]
   Google Scholar
• Edwards , O. E. and Grieco , C. 1974 . SN2 displacement at tertiary carbon . Can. J. Chem. , 52 : 3561
   Google Scholar
• Watanabe , M. , Okada , H. , Teshima , T. , Noguchi , M. and Kakehi , A. 1996 . A facile and regio‐ and stereoselective preparation of bicyclic guanidines by iodocyclization of 3‐(alk‐2‐enyl)‐2‐(substituted amino)‐1‐imidazolin‐4‐ones . Tetrahedron , 52 : 2827 [CROSSREF]
   Web of Science ®Google Scholar
• Chavan , S. P. , Zubaidha , P. K. and Dhondge , V. D. 1993 . A short and efficient synthesis of (−) mintlactone and (+) iso‐mintlactone . Tetrahedron , 49 : 6429 [CROSSREF]
   Google Scholar
• Greene , A. E. and Edgar , M. T. 1989 . Synthesis of oxoisodehydroleucodin: a novel guaianolide from Montanoa imbricata . J. Org. Chem. , 54 : 1468
   Google Scholar