Diastereoselective synthesis of cyclohexadienes via tandem cyclization strategies

Abdolali Alizadeh; Akram Bagherinejad; Fahimeh Bayat; Seyed Yasub Hosseini; Long-Guan Zhu

doi:10.1007/s11030-018-9900-x

Diastereoselective synthesis of cyclohexadienes via tandem cyclization strategies

Mol Divers. 2019 Aug;23(3):651-656. doi: 10.1007/s11030-018-9900-x. Epub 2018 Dec 5.

Authors

Abdolali Alizadeh¹, Akram Bagherinejad², Fahimeh Bayat², Seyed Yasub Hosseini², Long-Guan Zhu³

Affiliations

¹ Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran. aalizadeh@modares.ac.ir.
² Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran.
³ Department of Chemistry, Zhejiang University, Hangzhou, 310027, People's Republic of China.

PMID: 30519777
DOI: 10.1007/s11030-018-9900-x

Abstract

A new protocol has been developed for the diastereoselective synthesis of 1,3-cyclohexadienes using vinyl malononitriles, dibenzalacetones and NaH as reagents in THF. This transformation is comprised of interesting steps like Michael addition, cyclization and ring-opening reactions.

Keywords: 1,3-Cyclohexadienes; Cyclization; Dibenzalacetones; Michael addition; Ring-opening reaction; Vinyl malononitriles.

MeSH terms

Catalysis
Chemistry Techniques, Synthetic
Cyclization
Cyclohexenes / chemical synthesis*
Cyclohexenes / chemistry*
Stereoisomerism

Substances

Cyclohexenes