Tandem 5-exo-dig-5-exo-trig radical cyclization leading to a 6,5-ring fused carbobicycle possessing two contiguous quaternary carbons at the bridgehead and its adjacent positions

Journal of Chemical Research - Part S

Volumn , Issue 5, 1999, Pages 338-339

  Nagano, Hajime ^a   Ohtani, Yohko ^a   Odake, Eiko ^a   Nakagawa, Junko ^a   Mori, Yukie ^a,b   Yajima, Tomoko ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; BROMINE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033010996     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900444k     Document Type: Article

References (20)

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2. For reviews see: T.-L. Ho. Tandem Organic Reactions, Wiley, New York, 1992; R. A. Bunce, Tetrahedron, 1995, 51, 13103; L. F. Tietze, Chem. Rev., 1996, 96, 115; P. J. Parsons, C. S. Penkelt and A. J. Shell, Chem. Rev., 1996, 96, 195; M. Malacria, Chem. Rev., 1996, 96, 289; S. Handa and G. Pattenden, Contemp. Org. Synth., 1997, 4 196.
3. For reviews see: T.-L. Ho. Tandem Organic Reactions, Wiley, New York, 1992; R. A. Bunce, Tetrahedron, 1995, 51, 13103; L. F. Tietze, Chem. Rev., 1996, 96, 115; P. J. Parsons, C. S. Penkelt and A. J. Shell, Chem. Rev., 1996, 96, 195; M. Malacria, Chem. Rev., 1996, 96, 289; S. Handa and G. Pattenden, Contemp. Org. Synth., 1997, 4 196.
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19. No attempt was made to determine the stereochemistry of the inseparable dibromoacetals and cyclization products.
20. 3SnH gave two 5-exo-dig-5-exo-trig and a 5-exo-dig-6-(formal)-endo-trig cyclization products.