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Stereoselection in the Prins-Pinacol Synthesis of Acyltetrahydrofurans

Cohen, Frederick and MacMillan, David W. C. and Overman, Larry E. and Romero, Alex (2001) Stereoselection in the Prins-Pinacol Synthesis of Acyltetrahydrofurans. Organic Letters, 3 (8). pp. 1225-1228. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20170726-065800973

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Abstract

Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol0157003DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol0157003PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ol0157003PublisherSupporting Information
Additional Information:© 2001 American Chemical Society. Received 12 February 2001. Published online 23 March 2001. Published in print 1 April 2001. This research was supported by a Javits Neuroscience Investigator Award from NIH NINDS (NS-12389). Merck, Pfizer, Roche Biosciences, and SmithKline Beecham provided additional support. NMR and mass spectra were determined using instruments acquired with the assistance of NSF and NIH shared instrumentation grants.
Funders:
Funding AgencyGrant Number
NIHNS-12389
MerckUNSPECIFIED
PfizerUNSPECIFIED
Roche BiosciencesUNSPECIFIED
Smithkline BeechamUNSPECIFIED
NSFUNSPECIFIED
Issue or Number:8
Record Number:CaltechAUTHORS:20170726-065800973
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170726-065800973
Official Citation:Stereoselection in the Prins-Pinacol Synthesis of Acyltetrahydrofurans Frederick Cohen, David W. C. MacMillan, Larry E. Overman, and Alex Romero Organic Letters 2001 3 (8), 1225-1228 DOI: 10.1021/ol0157003
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:79374
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Jul 2017 22:18
Last Modified:03 Oct 2019 18:19

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