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Silicon-directed aldol condensation. Evidence for a pseudorotational mechanism

Myers, Andrew G. and Widdowson, Katherine L. and Kukkola, Paivi J. (1992) Silicon-directed aldol condensation. Evidence for a pseudorotational mechanism. Journal of the American Chemical Society, 114 (7). pp. 2765-2767. ISSN 0002-7863. doi:10.1021/ja00033a088. https://resolver.caltech.edu/CaltechAUTHORS:20180724-152025187

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ja00033a088DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/ja00033a088PublisherSupporting Information
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.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
David and Lucile Packard FoundationUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Arnold and Mabel Beckman Laboratories of Chemical Synthesis8546
Issue or Number:7
DOI:10.1021/ja00033a088
Record Number:CaltechAUTHORS:20180724-152025187
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180724-152025187
Official Citation:Silicon-directed aldol condensation. Evidence for a pseudorotational mechanism Andrew G. Myers, Katherine L. Widdowson, and Paivi J. Kukkola Journal of the American Chemical Society 1992 114 (7), 2765-2767 DOI: 10.1021/ja00033a088
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88212
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:24 Jul 2018 22:58
Last Modified:16 Nov 2021 00:24

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