Published March 25, 1992
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Journal Article
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Silicon-directed aldol condensation. Evidence for a pseudorotational mechanism
Abstract
Mechanistic studies of the reaction of the (S)-prolinol-derived O-silyl ketene N,O-acetal 1 with aromatic aldehydes are reported. Experiments with three 0-silyl ketene N,O-acetals derived from different 1,2-amino alcohols are also described and lead to a coherent mechanistic picture involving pseudorotation of trigonal bipyramidal organosilicon intermediates.
Additional Information
© 1992 American Chemical Society. Received December 3, 1991. Generous financial assistance from the National Science Foundation and the David and Lucile Packard Foundation is gratefully acknowledged. We are indebted to Professor Kurt Mislow for helpful discussions.Attached Files
Supplemental Material - ja00033a088_si_001.pdf
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Additional details
- Eprint ID
- 88212
- Resolver ID
- CaltechAUTHORS:20180724-152025187
- NSF
- David and Lucile Packard Foundation
- Created
-
2018-07-24Created from EPrint's datestamp field
- Updated
-
2021-11-16Created from EPrint's last_modified field
- Other Numbering System Name
- Arnold and Mabel Beckman Laboratories of Chemical Synthesis
- Other Numbering System Identifier
- 8546