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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.

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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.

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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.
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David and Lucile Packard FoundationUNSPECIFIED
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Arnold and Mabel Beckman Laboratories of Chemical Synthesis8546
Issue or Number:7
Record Number:CaltechAUTHORS:20180724-152025187
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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
Deposited By: George Porter
Deposited On:24 Jul 2018 22:58
Last Modified:16 Nov 2021 00:24

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