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
. 2009 May 21;11(10):2125-8.
doi: 10.1021/ol900647s.

Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure

Ryuji Hayashi  1 , Richard P Hsung, John B Feltenberger, Andrew G Lohse
Affiliations

Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure

Ryuji Hayashi et al. Org Lett. .

Abstract

A regio- and stereoselective isomerization of allenamides is described, leading to preparations of de novo 2-amido-dienes and a tandem isomerization-6pi-electron electrocyclic ring-closure.

PubMed Disclaimer

Figures

Figure 1
Figure 1
X-Ray Structure of 2-Amido-Diene 10b.
Scheme 1
Scheme 1
Allene Isomerizations.
Scheme 2
Scheme 2
Regioselective α-Isomerizations.
Scheme 3
Scheme 3
3-Amido-Trienes and Pericyclic Ring-Closure.
Scheme 4
Scheme 4
A Tandem α-Isomerization–Pericyclic Ring-Closure.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Woodward RB, Hoffmann R. Angew. Chem. Int. Ed. 1969;8:781.
    1. Jensen F. J. Am. Chem. Soc. 1995;117:7487.
    2. Lewis DK, Cochran JC, Hossenlopp J, Miller D, Sweeney T. J. Phys. Chem. 1981;85:1787.

    1. For general reviews on allenes, see: Krause N, Hashmi ASK. Modern Allene Chemistry. Vol 1 and 2. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA; 2004.

    1. For some examples, see: Meier H, Schmitt M. Tetrahedron Lett. 1989:5873. Crandall JK, Paulson DR. J. Am. Chem. Soc. 1966;88:4302. Bloch R, Perchec PL, Conia J-M. Angew. Chem. Int. Ed. 1970;9:798. Jones M, Hendrick ME, Hardie JA. J. Org. Chem. 1971;36:3061. Patrick TB, Haynie EC, Probat WJ. Tetrahedron Lett. 1971;27:423. Lehrich F, Hopf H. Tetrahedron Lett. 1987;28:2697.

    1. For some examples, see: Tsuboi S, Masuda T, Takeda A. J. Org. Chem. 1982;47:4478. Peng W, Zhu S. Tetrahedron. 2003;59:4641. Al-Masum M, Yamamoto Y. J. Am. Chem. Soc. 1998;120:3809. Bibas H, Koch R, Wentrup C. J. Org. Chem. 1998;63:2619. Jacobs TL, Johnson RN. J. Am. Chem. Soc. 1960;82:6397. Buzas AK, Istrate FM, Gagosz F. Org. Lett. 2007;9:985. Trost BM, Kazmaier U. J. Am. Chem. Soc. 1992;114:7933. Guo C, Lu X. J. Chem. Soc. Perkin Trans. 1993;1:1921.

Publication types