A novel palladium-catalyzed asymmetric cyclocarbonylation of allylic alcohols to γ-butyrolactones

Chemistry - A European Journal

Volumn 3, Issue 3, 1997, Pages 417-423

  Yu, Wing Yiu ^a   Bensimon, Corinne ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

asymmetric synthesis; butyrolactones; carbonylations; catalyst system; palladium

Indexed keywords

EID: 0030950812     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030313     Document Type: Article

References (42)

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29. The gem-dialkyl effect was found in intramolecular reactions, where gem-dialkyl substitution on a chain connecting reacting functional groups was particularly effective in enhancing ring-closure or retarding ring-opening reations. a) R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. 1915, 1117, 1080; b) C. K. Ingold, E. W. Lanfear, J. F. Thorpe, ibid, 1923, 123, 3140; c) T. C. Bruice, F. C. Lightstone, J. Am. Chem. Soc. 1994, 116, 10 789 and references therein.
30. The gem-dialkyl effect was found in intramolecular reactions, where gem-dialkyl substitution on a chain connecting reacting functional groups was particularly effective in enhancing ring-closure or retarding ring-opening reations. a) R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. 1915, 1117, 1080; b) C. K. Ingold, E. W. Lanfear, J. F. Thorpe, ibid, 1923, 123, 3140; c) T. C. Bruice, F. C. Lightstone, J. Am. Chem. Soc. 1994, 116, 10 789 and references therein.
31. 3 as the shift reagent as well as by chiral gas chromatographic analysis.
32. 1H NMR spectroscopy. Irradiation of the methine proton caused an NOE enhancement of 3.1% at the methyl protons, 3.9% at the methylene protons, and 8.9% at the protons on the phenyl ring at the β-position (Scheme 6). No NOE enhancement was observed for anti-4. (Equation Presented)
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42. Crystallographic data (excluding structure factors) for the structure reported in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100005. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: Int. code +(1223)336-033; e-mail: teched@chemcrys.cam.ac.uk).