An improved protocol for the preparation of (S)-vinylglycine from (S)-methionine
447
References
Chowdhury AR, Boons G-J (2005) The synthesis of diaminopimelic
acid containing peptidoglycan fragments using metathesis cross
coupling. Tetrahedron Lett 46:1675–1678
Denmark SE, Liu JH-C, Muhuhi JM (2009) Total syntheses of
isodomoic acids G and H. J Am Chem Soc 131:14188–14189
Feng Y, Coward JK (2006) Prodrug forms of N-[(4-deoxy-4-amino-
Afzaliardakani A, Rapoport H (1980) L-Vinylglycine. J Org Chem
4
5:4817–4820
Agouridas K, Girodeau JM, Pineau R (1985) Syntheses of protected
vinylic amino acids by intermolecular Lewis acid-catalyzed Ene
reactions. Tetrahedron Lett 26:3115–3118
Angst C (1987) Stereoselective synthesis of b,c-unsaturated amino
acids. Pure Appl Chem 59:373–380
Aponick A, Dietz AL, Pearson WH (2008) 2-(3-Pyrrolin-1-yl)-1,4-
naphthoquinones: photoactivated alkylating agents. Eur J Org
Chem 4264-4276
Armstrong A, Challinor L, Moir JH (2007) Exploiting organocatal-
ysis: enantioselective synthesis of vinyl glycines by allylic
sulfimide[2, 3]sigmatropic rearrangement. Angew Chem Int Ed
Engl 46:5369–5372
Badorrey R, Cativiela C, DiazdeVillegas MD, Galvez JA (1997) A
convenient synthesis of L-a-vinylglycine from D-mannitol.
Synthesis 747-749
Baldwin JE, Haber SB, Hoskins C, Kruse LI (1977) Synthesis of b,c-
unsaturated amino acids. J Org Chem 42:1239–1241
Barton DHR, Crich D, Herve Y, Potier P, Thierry J (1985) The free-
radical chemistry of carboxylic esters of 2-selenopyridine-N-
oxide—a convenient synthesis of (L)-vinylglycine. Tetrahedron
1
0-methyl)pteroyl]glutamate-c-[w P(O)(OH)]-glutarate, a potent
inhibitor of folylpoly-c-glutamate synthetase: synthesis and
hydrolytic stability. J Med Chem 49:770–788
Fitzner JN, Pratt DV, Hopkins PB (1985) Synthesis of protected
racemic b,c-unsaturated-a-amino acids via c-phenylseleno-a, b-
unsaturated esters. Tetrahedron Lett 26:1959–1962
Friis P, Helboe P, Larsen PO (1974) Synthesis and resolution of
vinylglycine, a b,c-unsaturated a-amino acid. Acta Chem Scand
Ser B Org Chem Biochem 28:317–321
Greenlee WJ (1984) Synthesis of b,c-unsaturated amino-acids by the
Strecker reaction. J Org Chem 49:2632–2634
Griesbeck AG, Hirt J (1995) A photochemical route to vinylglycine
and a vinylglycine dipeptide. Liebigs Annalen 1995:1957–1961
Hallinan KO, Crout DHG, Errington W (1994) Simple synthesis ofL-
vinylglycine and D-vinylglycine 2-aminobut-3-enoic acid and
related amino acids. J Chem Soc-Perkin Trans 1:3537–3543
Hamon DPG, Massywestropp RA, Razzino P (1992) The asymmetric
synthesis of a-amino acids via the addition of Grignard-reagents
to imine derivatives. Tetrahedron 48:5163–5178
4
1:4347–4357
Hanessian S, Sahoo SP (1984) A novel and efficient synthesis of L-
vinylglycine. Tetrahedron Lett 25:1425–1428
¨
Heinzer F, Bellus D (1981) Uber einen neuartigen synthetischen
Beaulieu PL, Duceppe JS, Johnson C (1991) Synthesis of chiral
vinylglycines. J Org Chem 56:4196–4204
Ben-Ishahi D, Moshenberg R, Altmann J (1977) A new synthesis of
amino acids-II: amidoalkylation of olefins with glyoxylic acid
derivatives. Tetrahedron 33:1533–1542
Zugang zu b,c-unges a¨ ttigten a-Aminocarbons a¨ uren. Helv Chim
Acta 64:2279–2297
Howard-Jones AR, Elkins JM, Clifton IJ, Roach PL, Adlington RM,
Baldwin JE, Rutledge PJ (2007) Interactions of isopenicillin N
synthase with cyclopropyl-containing substrate analogues reveal
new mechanistic insight. Biochemistry 46:4755–4762
Humblet V, Misra P, Bhushan KR, Nasr K, Ko YS, Tsukamoto T,
Pannier N, Frangioni JV, Maison W (2009) Multivalent scaffolds
for affinity maturation of small molecule cell surface binders and
their application to prostate tumor targeting. J Med Chem
Berkowitz DB, Maiti G (2004) Following an ISES lead: the first
examples of asymmetric Ni(0)-mediated allylic amination. Org
Lett 6:2661–2664
Berkowitz DB, Smith MK (1996) A convenient synthesis of
L-a-vinylglycine from L-homoserine lactone. Synthesis 39-41
Berkowitz DB, Charette BD, Karukurichi KR, McFadden JM (2006)
a-Vinylic amino acids: occurrence, asymmetric synthesis, and
biochemical mechanisms. Tetrahedron Asymmetr 17:869–882
Bicknell AJ, Burton G, Elder JS (1988) Novel phosphorane and
phosphonate synthons for vinyl glycines. Tetrahedron Lett
5
2:544–550
Itaya T, Shimizu S, Nakagawa S, Morisue M (1994) Syntheses of
optically-active, protected and unprotected vinylglycines. Chem
Pharm Bull 42:1927–1930
Johnston M, Raines R, Chang M, Esaki N, Soda K, Walsh C (1981)
Mechanistic studies on the reactions of bacterial methionine c-
lyase with olefinic amino acids. Biochemistry 20:4325–4333
Kitamura T, Sato Y, Mori M (2004) Synthetic study of (?)-
anthramycin using ring-closing enyne metathesis and cross-
metathesis. Tetrahedron 60:9649–9657
Krol WJ, Mao SS, Steele DL, Townsend CA (1991) Stereochemical
correlation of proclavaminic acid and syntheses of erythro-L-b-
hydroxyornithine and threo-L-b-hydroxyornithine from an
improved vinylglycine synthon. J Org Chem 56:728–731
Marchand D, Martinez J, Cavelier F (2008) Straightforward synthesis
of chiral silylated amino acids through hydrosilylation. Eur J Org
Chem 2008:3107–3112
2
9:3361–3364
B u¨ chert M, Meinke S, Prenzel AHGP, Deppermann N, Maison W
2006) Azabicycloalkenes as synthetic intermediates—Synthesis
(
of azabicyclo[X. 3.0] alkane scaffolds. Org Lett 8:5553–5556
Capitani G, Tschopp M, Eliot AC, Kirsch JF, Gr u¨ tter MG (2005)
Structure of ACC synthase inactivated by the mechanism-based
inhibitor L-vinylglycine. FEBS Lett 579:2458–2462
Carrasco M, Jones RJ, Kamel S, Rapoport H, Thien T (1992) N-
(Benzyloxycarbonyl)-L-vinylglycine methyl ester. Organic
Synth 70:29–32
Castelhano AL, Horne S, Billedeau R, Krantz A (1986) Reactions of
an electrophilic glycine cation equivalent with Grignard-
reagents—a simple synthesis of b,c-unsaturated amino acids.
Tetrahedron Lett 27:2435–2438
Chandrasekhar S, Raza A, Takhi M (2002) Synthesis of unusual amino
acids: N-(tert-butoxycarbonyl)-L-vinyl glycine and N-(tert-butoxy-
carbonyl)-L-homophenylalanine. Tetrahedron Asymmetr 13:423–428
Chari RVJ, Wemple J (1979) A simple, efficient synthesis of b-
methylene phenylalanine. A new approach to the preparation of
b,c-unsaturated a-amino acid enzyme substrate analogs. Tetra-
hedron Lett 20:111–114
Meffre, P, Voquang, L, Voquang, Y, and Legoffic, F (1989) N-
(
Benzyloxycarbonyl)-L-vinylglycine methyl-ester from L-methi-
onine methyl-ester hydrochloride. Synth Commun 19:3457-
468
3
Misra P, Humblet V, Pannier N, Maison W, Frangioni JV (2007)
Production of multimeric prostate-specific membrane antigen
small-molecule radiotracers using a solid-phase Tc-99 m pre-
loading strategy. J Nucl Med 48:1379–1389
Chiou WH, Mizutani N, Ojima I (2007) Highly efficient synthesis of
azabicyclo[x.y.0]alkane amino acids and congeners by means of
Rh-catalyzed cyclohydrocarbonylation. J Org Chem 72:1871–
Mulzer J, Funk G (1995) Synthesis of optically-active b,c-unsaturated
N
a-amino-acids and of a,b-unsaturated c-amino acids—S 2-
1
882
123