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Design of a New Cascade Reaction for the Construction of Complex Acyclic Architecture: The Tandem Acyl-Claisen Rearrangement

Dong, Vy M. and MacMillan, David W. C. (2001) Design of a New Cascade Reaction for the Construction of Complex Acyclic Architecture: The Tandem Acyl-Claisen Rearrangement. Journal of the American Chemical Society, 123 (10). pp. 2448-2449. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170406-072008585

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Abstract

Tandem or domino reactions have long been established as powerful chemical tools for the rapid formation of complex cyclic and polycyclic architecture. Surprisingly, however, relatively few tandem strategies have been directed toward the production of acyclic structural motifs despite significant advances in the area of acyclic stereocontrol. In our recent study, we reported the development of the acyl-Claisen rearrangement, a catalytic [3,3]-bond reorganization that allows the stereoselective synthesis of α,β-disubstituted-γ,δ-unsaturated carbonyls. In this communication, we outline the development of the tandem acyl-Claisen reaction, a highly stereoselective three-component coupling that enables the rapid construction of complex acyclic systems in the context of 2,3,6-trisubstituted-1,7-dioxoheptane architecture (eq 1). This versatile cascade sequence is conducted by using simple allyl diamines and acid chlorides, chemicals that are widely available in a diverse range of structural formats. As such, we expect this tandem reaction to be of broad utility to a number of chemical fields that employ molecule construction including natural product and parallel medicinal agent synthesis.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja005925tDOIArticle
http://pubs.acs.org/doi/full/10.1021/ja005925tPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja005925tPublisherSupporting Information
Additional Information:© 2001 American Chemical Society. Received 27 December 2000. Published online 16 February 2001. Published in print 1 March 2001. V.M.D. is grateful for an NSF predoctoral fellowship. Financial support was provided by the NIH (R01 GM61214-01).
Funders:
Funding AgencyGrant Number
NIHR01 GM61214-01
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:10
Record Number:CaltechAUTHORS:20170406-072008585
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170406-072008585
Official Citation:Design of a New Cascade Reaction for the Construction of Complex Acyclic Architecture:  The Tandem Acyl-Claisen Rearrangement Vy M. Dong and David W. C. MacMillan Journal of the American Chemical Society 2001 123 (10), 2448-2449 DOI: 10.1021/ja005925t
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75771
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:06 Apr 2017 16:55
Last Modified:03 Oct 2019 16:54

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