Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2000 Nov 8;122(44):11031-11032.
doi: 10.1021/ja0055110. Epub 2000 Oct 21.

Organoselenium-Based Entry into Versatile, α-(2-Tributylstannyl)vinyl Amino Acids in Scalemic Form: A New Route to Vinyl Stannanes

Affiliations

Organoselenium-Based Entry into Versatile, α-(2-Tributylstannyl)vinyl Amino Acids in Scalemic Form: A New Route to Vinyl Stannanes

David B Berkowitz et al. J Am Chem Soc. .
No abstract available

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3<i><sup>a</sup></i>
Scheme 3a
aKey: (i) Pd2dba3, p-I-C6H4-NO2, THF (85%); (ii) DCl, D2O, Δ, then Dowex-50 (75%); (iii) I2, CCl4 (92%); (iv) H2C=CHSnBu3, Pd2dba3, Pfur3, NMP (65%) (v) DMAD, Δ then Br2, CCl4/KOtBu, DMF.

References

    1. Refs: Berkowitz DB, Jahng W-J, Pedersen ML. Bioorg Med Chem Lett. 1996;6:2151–2156.Elegant mechanistic work: Nanavati SM, Silverman RB. J Am Chem Soc. 1991;113:9341–9349.

    1. Schafmeister CE, Po J, Verdine GL. J Am Chem Soc. 2000;122:5891–5892.
    2. Yokum TS, Gauthier TJ, Hammer RP, McLaughlin ML. J Am Chem Soc. 1997;119:1167–1168.
    3. Altmann KH, Altmann E, Mutter M. Helv Chim Acta. 1992;75:1198–1210.
    4. Karle I, Balaram P. Biochemistry. 1990;29:6747–6756. - PubMed
    1. Jaun B, Tanaka M, Seiler P, Kühnle FNM, Braun C, Seebach D. Liebigs Ann/Recueil. 1997:1697–1710.
    2. Aubry A, Bayeul D, Précigoux G, Pantano M, Formaggio F, Crisma M, Toniolo C, Boesten WHJ, Schoemaker HE, Kamphuis J. J Chem Soc Perkin 2. 1994:525–529.
    1. Obrecht D, Altorfer M, Lehmann C, Schonholzer, Muller K. J Org Chem. 1996;61:4080–4086. - PubMed
    2. Wipf P, Hemgartner H. Helv Chim Acta. 1988;71:258–267.
    1. Mendel D, Ellman J, Schultz PG. J Am Chem Soc. 1993;115:4359–4360. See also: van Hest JCM, Kiick KL, Tirrell DA. J Am Chem Soc. 2000;122:1282–1288.

LinkOut - more resources