One-Carbon bridge stereocontrol in robinson annulations leading to bicyclo[3.3.1]nonanes

Organic Letters

Volumn 12, Issue 6, 2010, Pages 1232-1235

  Wang, Dong ^a   Crowe, William E ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BICYCLO(3.3.1)NONANE; CARBON; CYCLOHEXANONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS; CARBON; CYCLOHEXANONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77949820070     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1000878     Document Type: Article

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33. An attractive explanation, suggested by a reviewer, is that observed stereoselectivity could be accounted for by intramolecular proton transfer. A similar stereochemical argument was presented in Grossman, R. B.; Ley, S. V. Tetrahedron 1994. 50. 11553. (Figure Presented)
34. A mixture of 18a and 18b was prepared by methylation of the corresponding mixture of 3a and 3b.
35. With less than 3 equiv of base, decarboxylation without epimerization is observed.
36. Since the keto form predominated for cyano-substituted Robinson annulation products 21a and 21b, an epimerization reaction favoring 21a was not considered a promising prospect. When the initially attempted epimerization of 21a:21b led to an complex mixture of decomposition products, this reaction was not pursued further.
37. 5,6 is incorrect, since product stereochemistry was not confirmed by X-ray crystallography.
38. 3c-eThe second Robinson annulation of this sequence exhibits diastereoselectivity analogous to those described herein, favoring the diastereomer that places the one-carbon bridge substituent anti to the β-keto ester unit introduced in the reaction.(Figure Presented)