Efficient Preparation of Polyunsaturated
and Functionalized Acetylenic Ketones from Alkynylmanganese
Bromides

Gérard Cahiez; Olivier Gager; Alban Moyeux; Blandine Laboue-Bertrand

doi:10.1055/s-0030-1258329

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2010(24): 4213-4220
DOI: 10.1055/s-0030-1258329

PAPER

Efficient Preparation of Polyunsaturated and Functionalized Acetylenic Ketones from Alkynylmanganese Bromides

Gérard Cahiez*, Olivier Gager, Alban Moyeux, Blandine Laboue-Bertrand
SOSCOM, Unité CNRS - Université de Paris13 FRE3043, 74 Rue Marcel Cachin, 93017 Bobigny, France
Fax: +33(1)48387363; e-Mail: gerard.cahiez@univ-paris13.fr;

Further Information

Publication History

Received 14 September 2010
Publication Date:
15 November 2010 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

α,β-Acetylenic ketones are efficiently prepared, under mild conditions, by reacting alkynylmanganese compounds with acyl chlorides. The procedure is especially useful for preparing polyfunctionalized and polyunsaturated α,β-acetylenic ketones.

Key words

organomanganese - acylation - acetylenic ketones - acyl chlorides

References

For a review, see:
1a Bol’shedvorskaya RL. Vereschagin LI. Russ. Chem. Rev. 1973, 42: 225

Google Scholar
For a few recent selected references, see:
1b Maeda Y. Kakiuchi N. Matsumura S. Nishimura T. Kawamura T. Uemura S. J. Org. Chem. 2002, 67: 6718

Google Scholar
1c Kel’in AV. Gevorgyan V. J. Org. Chem. 2002, 67: 95

Google Scholar
1d Bagley MC. Dale JW. Bower J. Chem. Commun. 2002, 1682

Google Scholar
1e Perollier CP. Sorokin AB. Chem. Commun. 2002, 1548

Google Scholar
1f Rossi E. Abbiati G. Canevari V. Nava D. Arcadi A. Tetrahedron 2004, 60: 11391

Google Scholar
1g Alonso DA. Najera C. Pacheco MC. J. Org. Chem. 2004, 69: 1615

Google Scholar
1h Payette JN. Yamamoto H. Angew. Chem. Int. Ed. 2009, 48: 8060

Google Scholar
1i Said A. Youssef A. J. Chem. Res. 2009, 214

Google Scholar
1j Druais V. Hall MJ. Corsi C. Wendeborn SV. Meyer C. Cossy J. Org. Lett. 2009, 11: 935

Google Scholar
1k Sydnes LK. Holmelid B. Sengee M. Hanstein M. J. Org. Chem. 2009, 74: 3430

Google Scholar
1l Fang R. Su C.-Y. Zhao C. Phillips DL. Organometallics 2009, 28: 216

Google Scholar
1m Yoshikawa T. Mori S. Shindo M. J. Am. Chem. Soc. 2009, 131: 2092

Google Scholar
1n Jin T. Yang F. Liu C. Yamamoto Y. Chem. Commun. 2009, 3533

Google Scholar
1o Zhang Y. Chen Z. Xiao Y. Zhang J. Chem. Eur. J. 2009, 15: 5208

Google Scholar
1p Bai Y. Fang J. Ren J. Wang Z. Chem. Eur. J. 2009, 15: 8975

Google Scholar
1q Lakshmi BV. Kazmaier U. Synlett 2010, 407

Google Scholar
1r Baeza B. Casarrubios L. Gomez-Gallego M. Sierra MA. Olivan M. Organometallics 2010, 29: 1607

Google Scholar
1s Cao H. Jiang H. Mai R. Zhu S. Qi C. Adv. Synth. Catal. 2010, 143

Google Scholar
1t Shchukin AO. Vasil’ev AV. Grinenko EV. Russ. J. Org. Chem. 2010, 46: 82 ; see also references quoted therein

Google Scholar
2a Cahiez G. Manganese dioxide, In Encyclopedia of Reagents for Organic Synthesis Paquette L. Wiley; Chichester: 1995. p.199

Google Scholar
See also:
2b Aijou AN. Ferguson G. Tetrahedron Lett. 2006, 47: 3719

Google Scholar
2c Maeda Y. Kakiuchi N. Matsumura S. Nishimura T. Kawamura T. Uemura S. J. Org. Chem. 2002, 67: 6718 ; and references quoted therein

Google Scholar
3 Dieter RK. Tetrahedron 1999, 55: 4177

Crossref Google Scholar
4a Birkofer L. Ritter A. Uhlenbrauck H. Chem. Ber. 1963, 96: 3280

Google Scholar
4b Walton DRM. Waugh FG.
J. Organomet. Chem. 1972, 37: 45

Google Scholar
4c Ladika M. Stang PJ. Chem. Commun. 1981, 459

Google Scholar
4d Yadav JS. Reddy BVS. Reddy MS. Synthesis 2003, 1722

Google Scholar
5a Chowdhury C. Kundu NG. Tetrahedron 1999, 55: 7011

Google Scholar
5b Guo M. Li D. Zhang Z. J. Org. Chem. 2003, 68: 10172

Google Scholar
5c Chen L. Li C.-J. Org. Lett. 2004, 6: 3151

Google Scholar
5d Cox RJ. Ritson DJ. Dane TA. Berge J. Charmant JPH. Kantacha A. Chem. Commun. 2005, 1037

Google Scholar
5e Lee KY. Lee MJ. Kim JN. Tetrahedron 2005, 61: 8705 ; see also references quoted therein

Google Scholar
For reviews on the chemistry of organomanganese reagents, see:
6a Cahiez G. An. Quim. 1995, 91: 561

Google Scholar
6b Cahiez G. Duplais C. Buendia J. Chem. Rev. 2009, 109: 1434

Google Scholar
7a Cahiez G. Masuda A. Bernard D. Normant J.-F. Tetrahedron Lett. 1976, 3155

Google Scholar
7b Cahiez G. Bernard D. Normant J.-F. Synthesis 1977, 130

Google Scholar
7c Cahiez G. Normant J.-F. Bull. Soc. Chim. Fr. 1977, 570

Google Scholar
7d Cahiez G. Tetrahedron Lett. 1981, 22: 1239

Google Scholar
7e Friour G. Alexakis A. Cahiez G. Normant J.-F. Tetrahedron 1984, 40: 683

Google Scholar
7f Friour G. Cahiez G. Normant J.-F. Synthesis 1984, 37

Google Scholar
7g Friour G. Cahiez G. Normant JF. Synthesis 1985, 50

Google Scholar
7h Cahiez G. Rivas-Enterrios J. Granger-Veyron H. Tetrahedron Lett. 1986, 27: 4441

Google Scholar
7i Cahiez G. Rivas-Enterrios J. Cléry P. Tetrahedron Lett. 1988, 30: 3659

Google Scholar
7j Klement I. Stadmüller H. Knochel P. Cahiez G. Tetrahedron Lett. 1977, 38: 1927

Google Scholar
8a Cahiez G. Laboue B. Tetrahedron Lett. 1989, 30: 3545

Google Scholar
8b Cahiez G. Laboue B. Tetrahedron Lett. 1992, 33: 4439

Google Scholar
8c Cahiez G. Chavant P.-Y. Métais E. Tetrahedron Lett. 1992, 33: 5245

Google Scholar
8d Cahiez G. Métais E. Tetrahedron Lett. 1995, 36: 6449

Google Scholar
8e Cahiez G. Métais E. Tetrahedron: Asymmetry 1996, 8: 1373

Google Scholar
8f Cahiez G. Razafintsalama L. Laboue B. Chau F. Tetrahedron Lett. 1998, 39: 849

Google Scholar
9 Cahiez G. Laboue B. Tetrahedron Lett. 1989, 30: 3545

Crossref Google Scholar