Mechanistic aspects of the lycopodine Michael-Claisen domino cyclization

Eger, Wilhelm A., Anders, Ernst and Williams, Craig M. (2014) Mechanistic aspects of the lycopodine Michael-Claisen domino cyclization. Journal of Molecular Modeling, 20 (Online First) 4: 2173.1-2173.8. doi:10.1007/s00894-014-2173-0

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Author Eger, Wilhelm A.
Anders, Ernst
Williams, Craig M.
Title Mechanistic aspects of the lycopodine Michael-Claisen domino cyclization
Journal name Journal of Molecular Modeling   Check publisher's open access policy
ISSN 1610-2940
0948-5023
0949-183X
Publication date 2014-03-16
Sub-type Article (original research)
DOI 10.1007/s00894-014-2173-0
Volume 20 (Online First)
Issue 4
Start page 2173.1
End page 2173.8
Total pages 8
Place of publication Heidelberg, Germany
Publisher Springer
Collection year 2015
Language eng
Formatted abstract
The Michael-Claisen domino (MCD) cyclization used in the lycopodine synthesis by Stork, was evaluated mechanistically using DFT calculations. Calculations suggest that a dianion is not formed, which conforms to classical dianion formation normally requiring strong kinetic bases. Instead ethoxide in ethanol produces a monoanionic species driving the MCD cyclization. This endeavor has opened up potential to expand the scope of this unique reaction and provide educational clarity.
Keyword Density functional theory
Lycopodine
Michael-Claisen cyclization
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes This paper belongs to a Topical Collection on the occasion of Prof. Tim Clark’s 65th birthday.

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 21 Mar 2014, 20:44:52 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences