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Synthesis 2006(5): 880-884
DOI: 10.1055/s-2006-926320
DOI: 10.1055/s-2006-926320
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of (±)-(2-Methylenecyclopropyl)glycine and (±)-4-[(Amino(carboxymethyl)]spiro[2.2]pentane-1-carboxylic Acid
Weitere Informationen
Received
1 September 2005
Publikationsdatum:
07. Februar 2006 (online)
Publikationsverlauf
Publikationsdatum:
07. Februar 2006 (online)

Abstract
A facile method for the preparation of racemic cyclopropylglycines is described, involving oxidation of cyclopropylcarbinols followed by a Bucherer-Berg reaction with sequential hydrolysis of the hydantoins obtained.
Key words
[1+2] cycloaddition - Bucherer-Berg reaction - cyclopropylglycines - carbenes - diazo compounds
- 1a
Salaün J.Baird MS. Curr. Med. Chem. 1995, 2: 511 - 1b
Salaün J. Top. Curr. Chem. 2000, 207: 1 - 1c
Stammer CH. Tetrahedron 1990, 46: 2231 - 2a
Vidal-Cros A.Bory S.Gaudry M.Marquet A. Tetrahedron Lett. 1989, 30: 1799 - 2b
Grigg R.Armstrong WP. Tetrahedron 1988, 44: 1523 - 2c
Baldwin JE.Adlington RM.Domayne-Hayman BP.Knight G.Ting H.-H. J. Chem. Soc., Chem. Commun. 1987, 1661 - 2d
Shoji J.-I.Sakazaki R.Kato Y.Yoshimura S.Matsuura Y.Tori J. Antibiotics 1981, 34: 370 - 2e
Kato K.Takita T.Umezawa H. Tetrahedron Lett. 1980, 21: 4925 - 2f
Yamanoi K.Ohfune Y.Watanabe K.Li PN.Takauchi H. Tetrahedron Lett. 1988, 29: 1181 - 2g
Shimamoto K.Ohfune Y. Tetrahedron Lett. 1990, 31: 4029 - 3
Wagner I.Musso H. Angew. Chem., Int. Ed. Engl. 1983, 22: 816 ; Angew. Chem. 1983, 95, 827 - 4a
Ma D.Zhu W. J. Org. Chem. 2001, 66: 348 - 4b
Hallinan KO.Crout DHG.Errington W. J. Chem. Soc., Perkin Trans. 1 1994, 3537 - 4c
Ma D.Ma Z.Jian J.Zheng C. Tetrahedron: Asymmetry 1997, 8: 889 - 4d
Shimamoto K.Ishida M.Shinozaki H.Ohfune J. J. Org. Chem. 1991, 56: 4167 - 4e
Pelliciari R.Natalini B.Marinozzi M.Monahan JB.Snyder JS. Tetrahedron Lett. 1990, 3: 139 - 4f
Pellicciari R.Marinozzi M.Constantino G.Natalini B.Moroni F.Pellegrini-Giampietro D. J. Med. Chem. 1999, 42: 2716 - 4g
Shimamoto K.Ohfune Y. J. Med. Chem. 1996, 39: 407 - 5a
Demir AS.Tanyeli C.Cagir A.Tahir MN.Ulku D. Tetrahedron: Asymmetry 1998, 9: 1035 - 5b
Ma D.Ma Z. Tetrahedron Lett. 1997, 38: 7599 - 5c
Monn JA.Valli MJ.Massey SM.Wright RA.Salhoff CR.Jonson BG.Howe T.Alt CA.Rhodes CA.Robey RL.Criffey KR.Tizzano JP.Kallman MJ.Helton DR.Schoepp DD. J. Med. Chem. 1997, 40: 528 - 5d
Ma D.Jiang Y. Tetrahedron: Asymmetry 2000, 11: 3727 - 5e
Ma D.Cao Y.Wu W.Jiang J. Tetrahedron 2000, 56: 7447 - 6a
Chavan SP.Venkatraman MS.Sharma AK.Chittiboyina AG. Tetrahedron Lett. 1996, 37: 2857 - 6b
Joucla M.el Goumzili M.Fouchet B. Tetrahedron Lett. 1986, 27: 1677 - 6c
Zindel J.de Meijere A. Synthesis 1994, 190 - 6d
Mazon A.Pedregal C.Prowse W. Tetrahedron 1999, 55: 7057 - 6e
Shibuya A.Kurishita M.Ago C.Taguchi T. Tetrahedron 1996, 52: 271 - 6f
Godula K.Donaldson WA. Tetrahedron Lett. 2001, 42: 153 - 6g
Horwell DC.McKierman MJ.Osborne S. Tetrahedron Lett. 1998, 39: 8729 - 7a
de Meijere A.Ernst K.Zuck B.Brandl M.Kozhushkov SI.Tamm M.Yufit DS.Howard JAK.Labahn T. Eur. J. Org. Chem. 1999, 3105 - 7b
Wessjohann I.Krass N.Yu D.de Meijere A. Chem. Ber. 1992, 125: 867 - 8
Averina EB.Yashin NV.Kuznetsova TS.Zefirov NS. Vestn. Mosk. Univ., Ser. 2: Khim. 2002, 43: 246 ; Chem. Abstr. 2002, 138, 254854 - 9
Kurokawa N.Ohfune Y. Tetrahedron Lett. 1985, 26: 83 - 10a
Ahachinskaya TV.Donskaya NA.Kalyakina IV.Oprunenko YuF.Shabarov YuS. Zh. Org. Khim. 1989, 25: 1645 ; Chem. Abstr. 1990, 112, 178151 - 10b
Heiner T.Kozhushkov SI.Noltemeyer M.Haumann T.Boese R.de Meijere A. Tetrahedron 1996, 52: 12185 - 11a
Carbon JA.Martin WB.Sweet LR. J. Am. Chem. Soc. 1958, 80: 1002 - 11b
Lai M.Liu L.Liu H. J. Am. Chem. Soc. 1991, 113: 7388 - 12
Le Core M.Hercouet A.Bessieres B. J. Org. Chem. 1994, 59: 5483 - 13a
Ware E. Chem. Rev. 1950, 46: 403 - 13b
Christensen HN.Handlogten ME.Lam I.Tager HS.Zand R. J. Biol. Chem. 1969, 244: 1510 - 14
Corey EJ.Suggs JW. Tetrahedron Lett. 1975, 30: 2647