Volume 119, Issue 48 pp. 9455-9457

Zuschrift

All-Carbon Intramolecular Conjugate Displacement Reactions: An Effective Route to Carbocycles^†

Bodhuri Prabhudas Dr.,

Bodhuri Prabhudas Dr.

Chemistry Department, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada, Fax: (+1) 780-492-8231

Search for more papers by this author

Derrick L. J. Clive Prof. Dr.,

Derrick L. J. Clive Prof. Dr.

[email protected]

Chemistry Department, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada, Fax: (+1) 780-492-8231

Search for more papers by this author

Bodhuri Prabhudas Dr.,

Bodhuri Prabhudas Dr.

Chemistry Department, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada, Fax: (+1) 780-492-8231

Search for more papers by this author

Derrick L. J. Clive Prof. Dr.,

Derrick L. J. Clive Prof. Dr.

[email protected]

Chemistry Department, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada, Fax: (+1) 780-492-8231

Search for more papers by this author

First published: 05 December 2007

https://doi.org/10.1002/ange.200703022

Citations: 4

^†

We thank the NSERC for financial support, E. J. L. Stoffman for assistance, and Dr. R. McDonald for the X-ray determination.

Share a link

Email
Wechat
Bluesky

Graphical Abstract

Kooperation: Durch Michael-Addition und S_N2′-Reaktion können stabilisierte Carbanionen oder nucleophile Kohlenstoffatome von Enaminen intramolekular an α,β-ungesättigte Esterfunktionen addieren, die in Allylstellung eine Abgangsgruppe tragen (siehe Schema); als Produkte entstehen ungesättigte Carbocyclen. Die benötigten Ester sind durch eine Selen-vermittelte Alternative zur klassischen Baylis-Hillman-Reaktion zugänglich.

Supporting Information

References

1D. L. J. Clive, M. Yu, Z. Li, Chem. Commun. 2005, 906–908.
10.1039/b413481h
CAS PubMed Web of Science® Google Scholar
2D. L. J. Clive, Z. Li, M. Yu, J. Org. Chem. 2007, 72, 5608–5617.
10.1021/jo070664s
CAS PubMed Web of Science® Google Scholar
3Reviews of Baylis–Hillman reactions:
Google Scholar
3aD. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811–891;
10.1021/cr010043d
CAS PubMed Web of Science® Google Scholar
3bK. Y. Lee, S. Gowrisankar, J. N. Kim, Bull. Korean Chem. Soc. 2005, 26, 1481–1490.
10.5012/bkcs.2005.26.10.1481
CAS Web of Science® Google Scholar
4Under standard Baylis–Hillman conditions (1,4-diazabicyclo[2.2.2]octane (DABCO), room temperature, 2 days), 7 gave a complex mixture. The selenium-based method is a reliable alternative to the classical Baylis–Hillman procedure; see
Google Scholar
4areference [2];
Google Scholar
4bS.-R. Sheng, Q. Wang, Q.-Y. Wang, L. Guo, X. Huang, Synlett 2006, 1887–1890;
10.1055/s-2006-947341
CAS Web of Science® Google Scholar
4cI. Shiina, Y. Yamai, T. Shimazaki, J. Org. Chem. 2005, 70, 8103–8106.
10.1021/jo051276y
CAS PubMed Web of Science® Google Scholar
5For the use of vinylalanes to generate Baylis–Hillman adducts, see:
Google Scholar
5aP. V. Ramachandran, M. T. Rudd, T. E. Burghardt, M. V. R. Reddy, J. Org. Chem. 2003, 68, 9310–9316;
10.1021/jo034954u
CAS PubMed Web of Science® Google Scholar
5bT. Tsuda, T. Yoshida, T. Saegusa, J. Org. Chem. 1988, 53, 1037–1040.
10.1021/jo00240a020
CAS Web of Science® Google Scholar
6For examples of carbon-based intermolecular conjugate displacements, see:
Google Scholar
6aA. Chamakh, H. Amri, Tetrahedron Lett. 1998, 39, 375–378;
10.1016/S0040-4039(97)10593-7
CAS Web of Science® Google Scholar
6breference [3b].
Google Scholar
7
7aP. Knochel, D. Seebach, Nouv. J. Chim. 1981, 5, 75–77;
CAS Web of Science® Google Scholar
7bP. Knochel, D. Seebach, Tetrahedron Lett. 1981, 22, 3223–3226;
10.1016/S0040-4039(01)81868-2
CAS Web of Science® Google Scholar
7cD. Seebach, P. Knochel, Helv. Chim. Acta 1984, 67, 261–283;
10.1002/hlca.19840670133
CAS Web of Science® Google Scholar
7dD. Seebach, G. Calderari, P. Knochel, Tetrahedron 1985, 41, 4861–4872.
10.1016/S0040-4020(01)96725-0
CAS Web of Science® Google Scholar
8
8aY. Hayashi, H. Gotoh, T. Tamura, H. Yamaguchi, R. Masui, M. Shoji, J. Am. Chem. Soc. 2005, 127, 16028–16029;
10.1021/ja055740s
CAS PubMed Web of Science® Google Scholar
8bIn this preliminary study, we have not evaluated the ee value of 14 a. See also: W. J. Yang, M. T. Hechavarria Fonseca, B. List, J. Am. Chem. Soc. 2005, 127, 15036–15037.
10.1021/ja055735o
CAS PubMed Web of Science® Google Scholar
9
9aC.-W. Cho, J.-R. Kong, M. J. Krische, Org. Lett. 2004, 6, 1337–1339;
10.1021/ol049600j
CAS PubMed Web of Science® Google Scholar
9bS. E. Drewes, M. M. Horn, N. Ramesar, Synth. Commun. 2000, 30, 1045–1055;
10.1080/00397910008087122
CAS Web of Science® Google Scholar
9cY. M. Chung, J. H. Gong, T. H. Kim, J. N. Kim, Tetrahedron Lett. 2001, 42, 9023–9026;
10.1016/S0040-4039(01)01971-2
CAS Web of Science® Google Scholar
9dY. J. Im, J. M. Kim, J. H. Mun, J. N. Kim, Bull. Korean Chem. Soc. 2001, 22, 349–350.
CAS Web of Science® Google Scholar
10We did not observe any transient intermediates but appreciate that 17 a might also be formed from 17 b.
Google Scholar
11Review on CP molecules: D. A. Spiegel, J. T. Njardarson, I. M. McDonald, J. L. Wood, Chem. Rev. 2003, 103, 2691–2727.
10.1021/cr020408+
CAS PubMed Web of Science® Google Scholar
12See the Supporting Information.
Google Scholar
13For the rare radical analogue of an ICD reaction, see: I. W. Harvey, H. H. Whitham, J. Chem. Soc. Perkin Trans. 1 1993, 191–196.
10.1039/p19930000191
CAS Web of Science® Google Scholar
14Y.-G. Suh, J.-K. Jung, S.-A. Kim, D.-Y. Shin, K.-H Min, Tetrahedron Lett. 1997, 38, 3911–3914.
10.1016/S0040-4039(97)00777-6
CAS Web of Science® Google Scholar
15
15aB. M. Trost, Angew. Chem. 1989, 101, 1199–1219;
10.1002/ange.19891010906
CAS Google Scholar
Angew. Chem. Int. Ed. Engl. 1989, 28, 1173–1192;
10.1002/anie.198911731
Web of Science® Google Scholar
15bA. Heumann, M. Réglier, Tetrahedron 1995, 51, 975–1015;
10.1016/0040-4020(94)01011-N
CAS Web of Science® Google Scholar
15cB. M. Trost, J. D. Oslob, J. Am. Chem. Soc. 1999, 121, 3057–3064;
10.1021/ja983617d
CAS Web of Science® Google Scholar
15dB. M. Trost, S. J. Brickner, J. Am. Chem. Soc. 1983, 105, 568–575.
10.1021/ja00341a043
CAS Web of Science® Google Scholar

Citing Literature

Volume119, Issue48

December 10, 2007

Pages 9455-9457

This is the

German version

of Angewandte Chemie.

Note for articles published since 1962:

Do not cite this version alone.

Take me to the International Edition version with citable page numbers, DOI, and citation export.

We apologize for the inconvenience.

All-Carbon Intramolecular Conjugate Displacement Reactions: An Effective Route to Carbocycles^†

Graphical Abstract

Supporting Information

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

All-Carbon Intramolecular Conjugate Displacement Reactions: An Effective Route to Carbocycles†

Graphical Abstract

Supporting Information

References

Citing Literature

References

Related

Information

All-Carbon Intramolecular Conjugate Displacement Reactions: An Effective Route to Carbocycles^†