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. 2004 Aug 5;6(16):2661-4.
doi: 10.1021/ol049159x.

Following an ISES lead: the first examples of asymmetric Ni(0)-mediated allylic amination

David B Berkowitz  1 , Gourhari Maiti
Affiliations

Following an ISES lead: the first examples of asymmetric Ni(0)-mediated allylic amination

David B Berkowitz et al. Org Lett. .

Abstract

An ISES (in situ enzymatic screening) lead pointed to conditions (PMP N-protecting group, Ni(cod)(2) catalyst precursor) under which chiral, bidentate phosphines could promote Ni(0)-mediated allylic amination. Therefore, bidentate phosphines bearing central, axial, and planar chirality were examined with two model substrates of interest for PLP-enzyme inhibitor synthesis. In the best case, with (R)-MeO-BIPHEP, vinylglycinol derivative 2 was obtained in 75% ee (97% ee, one recrystallization) from 1. Further manipulation provided a Ni(0)-mediated entry into l-vinylglycine. [reaction: see text]

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Figures

Figure 1
Figure 1
UV/vis Traces for the ISES Data in Table 1.
Figure 2
Figure 2
Array of Chiral Bidentate Phosphine Ligands Examined
Scheme 1
Scheme 1
Synthesis of the Vigabatrin Precursor
Scheme 2
Scheme 2
A Ni(0)-Mediated Synthesis of L-Vinylglycine
See this image and copyright information in PMC

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References

    1. Berkowitz DB, Jahng W-J, Pedersen ML. Bioorg Med Chem Lett. 1996;6:2151–2156. and references therein. - PMC - PubMed

    1. Inhibition studies: Liang F, Kirsch JF. Biochemistry. 2000;39:2436–2444.Zheng L, White RH, Cash VL, Dean DR. Biochemistry. 1994;33:4714–20.Asada Y, Tanizawa K, Yonaha K, Soda K. Agric Biol Chem. 1988;52:2873–2878.Gehring H, Rando RR, Christen P. Biochemistry. 1977;16:4832–4836.Soper TS, Manning JM, Marcotte PA, Walsh CT. J Biol Chem. 1977;252:1571–1575.

    1. Jung MJ, Palfreyman MG. Vigabatrin. In: Levy RH, Mattson RH, editors. Antiepileptic Drugs. 4. Raven; New York: 1995.
    1. Brodie JD, Figueroa E, Dewey SL. Synapse. 2003;50:261–265. - PubMed
    2. Gerasimov MR, Dewey SL. Drug Dev Res. 2003;59:240–248.

    1. L-Vinylglycine: Rose NGW, Blaskovich MA, Wong A, Lajoie GA. Tetrahedron. 2001;57:1497–1507.Campbell AD, Raynam TM, Taylor RJK. Synthesis. 1998:1707–1709.Badorrey R, Cativiela C, Diaz-de-Villegas MD, Galvez JA. Synthesis. 1997:747–749.Berkowitz DB, Smith MK. Synthesis. 1996:39–41.Griesbeck AG. Hirt, J Liebigs Ann. 1995:1957–1961.Hallinan KO, Crout DHG, Errington W. J C S Perkin 1. 1994:3537–3543.Carrasco M, Jones RJ, Kamel S, Rapoport H, Truong T. Org Synth. 1991;70:29–34.Pellicciari R, Natalini B, Marinozzi M. Synthetic Commun. 1988;18:1715–1721.Duhamel L, Duhamel P, Fouquay S, Eddine JJ, Peschard O, Plaquevent JC, Ravard A, Solliard R, Valnot JY, Vincens H. Tetrahedron. 1988;44:5495–5506.Barton DHR, Crich D, Herve Y, Potier P, Thierry J. Tetrahedron. 1985;41:4347–4357.Hanessian S, Sahoo SP. Tetrahedron Lett. 1984;25:1425–1428.Schöllkopf U, Nozulak J, Groth U. Tetrahedron. 1984;40:1409–1417.

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