Rhodium Complex-Catalyzed Cycloisomerization of Allenenes: Exo and Endo Cyclization Depending on the Auxiliary Ligands

Journal of Organic Chemistry

Volumn 69, Issue 2, 2004, Pages 395-405

  Makino, Tatsuya ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ISOMERIZATION; RHODIUM COMPOUNDS; STEREOCHEMISTRY;

CYCLIZATIONS; CYCLOISOMERIZATION;

ORGANIC COMPOUNDS;

ALLENE DERIVATIVE; ALLENENE DERIVATIVE; LIGAND; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION; OXIDATION; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0345871949     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035551x     Document Type: Article

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192. Previously, Trost et al. investigated the related ruthenium-catalyzed intermolecular couplings of allenes and alkenes derived from vinyl ketones to provide 1,3-dienes, see: (a) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 4068-4069.
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195. The conversion and the purity were determined by GC analysis of the reaction mixture and the isolated product 2, respectively. The recovered allenene 1 was included in the impurity.
196. Almost pure 6 was readily obtained by recrystallization from ethyl acetate/n-hexane.
197. Siverstein, R. M.; Webster, F. X. Spectrometric Identification of Organic Compounds, 6th ed.; Wiley: New York, 1998.
198. For recent examples, see the following. Pd: (a) Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615-2616.
199. (b) Oh, C. H.; Yoo, H. S.; Jung, S. H. Chem. Lett. 2001, 1288-1289.
200. In the case of the rhodium-catalyzed cycloisomerization of allenynes, the allene moiety coordinates to the rhodium(I) center at the external allenic π-bond to form the metallacycle intermediate, see refs 32a,b.
201. No isomerization of the Z isomer to the more thermodynamically stable E isomer was observed under the reaction conditions.
202. Similar observations were reported in the rhodium- and platinum-catalyzed [4+1] cycloaddition of vinylallenes and the iridium-catalyzed [5+1] cycloaddition of allenylcyclopropanes, see refs 27f,j,k.
203. Recently, Trost et al. reported the formation of exo-alkylidenecycloheptenes by the rutheniun-catalyzed cycloisomerization of 1,6-enynes, see refs 5c,e.
204. 2 behaved as an effective catalyst to give 34 in 74% yield.
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212. Desilylation of α-silyl ketone trans,cis-39 might proceed via the corresponding enol silyl ether under thermal or catalytic condition to provide trans-40, see: Matsuda, I.; Sato, S.; Hattori, M.; Izumi, Y. Tetrahedron Lett. 1985, 26, 3215-3218.
213. The stereochemistry for both trans,cis-39 and trans-40 was estimated from the NOESY spectra, respectively.
214. More increase of CO pressure inhibited incorporation of carbon monoxide to give undesirable isomers.
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216. (a) Kosolapoff, G. M. Organophosphorus Compounds; Wiley: New York, 1950.
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