A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes

Hong C. Shen; Jiashi Wang; Kevin P. Cole; Michael J. McLaughlin; Christopher D. Morgan; Christopher J. Douglas; Richard P. Hsung; Heather A. Coverdale; Aleksey I. Gerasyuto; Juliet M. Hahn; Jia Liu; Heather M. Sklenicka; Lin Li Wei; Luke R. Zehnder; Craig A. Zificsak

doi:10.1021/jo020688t

A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes

Hong C. Shen, Jiashi Wang, Kevin P. Cole, Michael J. McLaughlin, Christopher D. Morgan, Christopher J. Douglas, Richard P. Hsung, Heather A. Coverdale, Aleksey I. Gerasyuto, Juliet M. Hahn, Jia Liu, Heather M. Sklenicka, Lin Li Wei, Luke R. Zehnder, Craig A. Zificsak

Chemistry (Twin Cities)

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Abstract

A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of α,β-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6π-electron electrocyclic ring-closure of 1-oxatrienes.

Original language	English (US)
Pages (from-to)	1729-1735
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	68
Issue number	5
DOIs	https://doi.org/10.1021/jo020688t
State	Published - Mar 7 2003

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Shen, H. C., Wang, J., Cole, K. P., McLaughlin, M. J., Morgan, C. D., Douglas, C. J., Hsung, R. P., Coverdale, H. A., Gerasyuto, A. I., Hahn, J. M., Liu, J., Sklenicka, H. M., Wei, L. L., Zehnder, L. R., & Zificsak, C. A. (2003). A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes. Journal of Organic Chemistry, 68(5), 1729-1735. https://doi.org/10.1021/jo020688t

A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes. / Shen, Hong C.; Wang, Jiashi; Cole, Kevin P. et al.
In: Journal of Organic Chemistry, Vol. 68, No. 5, 07.03.2003, p. 1729-1735.

Research output: Contribution to journal › Article › peer-review

Shen, HC, Wang, J, Cole, KP, McLaughlin, MJ, Morgan, CD, Douglas, CJ, Hsung, RP, Coverdale, HA, Gerasyuto, AI, Hahn, JM, Liu, J, Sklenicka, HM, Wei, LL, Zehnder, LR & Zificsak, CA 2003, 'A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes', Journal of Organic Chemistry, vol. 68, no. 5, pp. 1729-1735. https://doi.org/10.1021/jo020688t

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title = "A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes",

abstract = "A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of α,β-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6π-electron electrocyclic ring-closure of 1-oxatrienes.",

author = "Shen, {Hong C.} and Jiashi Wang and Cole, {Kevin P.} and McLaughlin, {Michael J.} and Morgan, {Christopher D.} and Douglas, {Christopher J.} and Hsung, {Richard P.} and Coverdale, {Heather A.} and Gerasyuto, {Aleksey I.} and Hahn, {Juliet M.} and Jia Liu and Sklenicka, {Heather M.} and Wei, {Lin Li} and Zehnder, {Luke R.} and Zificsak, {Craig A.}",

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AU - Morgan, Christopher D.

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AU - Hsung, Richard P.

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A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes

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