Synthetic Optimization and Structural Limitations of the Nitrile Aldol Reaction

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6316-6321

  Carlier, Paul R ^a   Lo, Kam Moon ^a   Lo, Michael M C ^a   Lo, Priscilla C K ^a   Lo, Cedric W S ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001409660     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9702148     Document Type: Article

References (23)

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11. 3TiCl transmetalated lithiophenylacetonitrile to benzaldehyde in THF. Taking into consideration the fact that their assignment should be reversed (see ref 4b, footnote 5), the actual ratio they obtained corresponds to 0.85:1, essentially what we observe.
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13. Silverman et al. previously reported that application of their protocol to the reaction of phenylacetonitrile and benzaldehyde gave a single aldol product of unspecified relative configuration. However subsequent reexamination in our laboratory and in the Silverman group revealed the product to be approximately a 4:1 mixture of anti- and syn- diastereomers (private communication, R. B. Silverman to P. R. Carlier).
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20. +) for the epoxidation of cis-methyl cinnamate derivatives indicates that a carbocationic intermediate is not on the reaction path (Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martinez, L. E. Tetrahedron 1994, 50, 4323-4334.)
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