Michael initiated cascade reaction sequences and their application in target synthesis
Michael initiated cascade reaction sequences and their application in target synthesis
An approach to the Podophyllum lignans is described.
A convenient method for the diastereoselective synthesis of trisubstituted alkenes through the lithium amide mediated union of ketones and diethyl maleate is presented. The reaction has been shown to proceed via a Michael Initiated - Condensation - Elimination (MICE) sequence.
The course of MICE sequence can be altered dramatically when the lithium amide is pre-treated with TMSCl. With half an equivalent of this additive a Michael adduct is given. Employing three equivalents leads to a silyl enol ether in >85% yield. The addition of lithium dialkylamides to diethyl acetylenedicarboxylate has also been shown to proceed more smoothly and with enhanced selectivity when conducted in the presence of TMSCl.
A review of Michael initiated cascade reactions is also presented.
University of Southampton
1998
Poon, Hon-suen
(1998)
Michael initiated cascade reaction sequences and their application in target synthesis.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
An approach to the Podophyllum lignans is described.
A convenient method for the diastereoselective synthesis of trisubstituted alkenes through the lithium amide mediated union of ketones and diethyl maleate is presented. The reaction has been shown to proceed via a Michael Initiated - Condensation - Elimination (MICE) sequence.
The course of MICE sequence can be altered dramatically when the lithium amide is pre-treated with TMSCl. With half an equivalent of this additive a Michael adduct is given. Employing three equivalents leads to a silyl enol ether in >85% yield. The addition of lithium dialkylamides to diethyl acetylenedicarboxylate has also been shown to proceed more smoothly and with enhanced selectivity when conducted in the presence of TMSCl.
A review of Michael initiated cascade reactions is also presented.
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Published date: 1998
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Local EPrints ID: 463341
URI: http://eprints.soton.ac.uk/id/eprint/463341
PURE UUID: 54253ce2-6987-474c-9cf4-9104cbf5e64c
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Date deposited: 04 Jul 2022 20:50
Last modified: 04 Jul 2022 20:50
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Author:
Hon-suen Poon
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