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1,6-Conjugate addition initiated formal [4+2] annulation of p-quinone methides with sulfonyl allenols: a unique access to spiro[5.5]undeca-1,4-dien-3-one scaffolds

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Abstract

An expedient one-pot synthesis of carbocyclic spiro[5.5]undeca-1,4-dien-3-ones via 1,6-conjugate addition initiated formal [4+2] annulation sequences by employing p-quinone methides and sulfonyl allenols is presented. Furthermore, this synthetic protocol tolerates a wide variety of p-quinone methides and sulfonyl allenols and affords the corresponding structurally unique spiro[5.5]undeca-1,4-dien-3-ones in good yield under mild reaction conditions.

Graphical abstract: 1,6-Conjugate addition initiated formal [4+2] annulation of p-quinone methides with sulfonyl allenols: a unique access to spiro[5.5]undeca-1,4-dien-3-one scaffolds

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Article information


Submitted
11 Feb 2020
Accepted
18 Mar 2020
First published
24 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

1,6-Conjugate addition initiated formal [4+2] annulation of p-quinone methides with sulfonyl allenols: a unique access to spiro[5.5]undeca-1,4-dien-3-one scaffolds

G. S. Ghotekar, S. R. Shirsath, A. C. Shaikh and M. Muthukrishnan, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC01005G

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