Diastereoselective intramolecular temporary silicon-tethered rhodium-catalyzed [4+2+2] cycloisomerization reactions: Regiospecific incorporation of substituted 1,3-butadienes

Journal of the American Chemical Society

Volumn 126, Issue 36, 2004, Pages 11150-11151

  Evans, P Andrew ^a   Baum, Erich W ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; RHODIUM; SILICON;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; ISOMERIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 4544272375     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046030+     Document Type: Article

References (23)

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3. For another example of a rhodium-catalyzed [4+2+2] carbocyclization reaction, see: Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002. 124, 8784.
4. For related metal-catalyzed [4+2+2] carbocyclization reactions, see: (a) Greco, A.; Carbonaro, A.; Dall'Asta, G. J. Org. Chem. 1970, 35, 271.
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9. For examples of other rhodium-catalyzed carbocyclization reactions leading to eight-membered rings, see: (a) [6+2]: Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815.
10. (b) [5+2+1]: Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876.
11. Treatment of the 1,6-enyne i with piperylene iia gave no reaction, whereas isoprene iib afforded the cycloadducts iii/iv in 60% yield, as a 1:1 mixture of regioisomers. (diagram presented)
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14. For recent reviews on TST strategies, see: (a) White, J. D.; Carter, R. G. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations: Fleming, T., Ed.; Georg Thieme Verlag: New York, 2001; Vol. 4, pp 371-412.
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19. The 1,6-enyne (Z)-1 (where X = NTs, R = H) was prepared using the three-step protocol outlined below. Mitsunobu coupling of the allylic alcohol 5 with the propargyl sulfonamide 4 furnished the allylic sulfonamide 6. The tert-butyldimethylsilyl ether 6 was deprotected, and the primary alcohol coupled with the diene 7 to afford (Z)-1 in 87% overall yield (3 steps). (diagram presented)
20. This catalyst provided a general solution to the problem of diastereoselectivity in the intermolecular [4+2+2] carbocyclization of 3-substituted sulfonamide 1,6-enynes and 1,3-butadiene. Evans. P. A.; Fazal, A. N.; Baum, E. W. Manuscript in preparation.
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