Regio- and diastereoselective rhodium-catalyzed allylic substitution with acyclic α-alkoxy-substituted copper(I) enolates: Stereodivergent approach to 2,3,6-trisubstituted dihydropyrans

Journal of the American Chemical Society

Volumn 126, Issue 28, 2004, Pages 8642-8643

  Evans, P Andrew ^a   Lawler, Michael J ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; PYRAN DERIVATIVE; RHODIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; HYPOTHESIS; PHASE TRANSITION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 3242717499     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049080n     Document Type: Article

References (22)

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11. The unmodified lithium enolate results in poor conversion (22%) and diminished selectivity (2°:1° = 34:1, ds = 8:1).
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18. Although the phenyl ketones 3 undergo the analogous Baeyer-Villiger oxidation, the yields are approximately 20% lower as compared to those for the p-methoxy phenyl ketone derivative.12b
19. For a recent review on the stereoselective construction of cyclic ethers, see: Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913 and pertinent references therein.
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