Highly Enantioselective Imine Cinnamylation with a Remarkable Diastereochemical Switch

The first general method for the enantioselective cinnamylation of aldimines is reported. The method utilizes a simple chiral cinnamylsilane reagent and is characterized by experimental simplicity and extraordinarily high levels of enantioselectivity. Further, a remarkable and unprecedented diastere...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2007-11, Vol.129 (47), p.14552-14553
Main Authors: Huber, John D, Leighton, James L
Format: Article
Language:English
Subjects:
Benzene - chemistry
Cinnamates - chemistry
Imines - chemistry
Molecular Structure
Stereoisomerism
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Summary:The first general method for the enantioselective cinnamylation of aldimines is reported. The method utilizes a simple chiral cinnamylsilane reagent and is characterized by experimental simplicity and extraordinarily high levels of enantioselectivity. Further, a remarkable and unprecedented diastereochemical reversal has been realized whereby either diastereomer may be accessed from the same trans-cinnamylsilane based upon a subtle change to the imine, thus obviating the usual requirement for both the trans- and cis-cinnamylsilanes.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja076035h