A Unified Synthesis of Electron-Deficient 1,4- and 1,1,4-Substituted 1,3-Dienes through a Base-Promoted Allylation Followed by Retro-Michael Vinylogous Dehydrosulfinylation

Ayelet Rothstein, Lena Trifonov, Niv Keidar, Michal Afri, Edward E. Korshin, Arie Gruzman

Research output: Contribution to journalArticlepeer-review

Abstract

We disclose a general 2-step synthesis of electron-poor 1,4- and 1,1,4-substituted buta-1,3-dienes bearing electron-withdrawing substituents at both termini of the conjugated system. The method relies on a base-promoted C-allylation of primary or secondary alkylsulfones with γ-bromocrotonate or related amide, nitrile, or sulfone and subsequent vinylogous retro-Michael dehydrosulfinylation. The geometry of the resulting dienes is substrate-dependent, and predominantly E,E-dienes are formed from E-electrophiles. This phosphorus- and transition-metal-free method tolerates a variety of functionalities and could serve as a supplement to Wittig, HWE, and Julia olefinations.

Original languageEnglish
Pages (from-to)8565-8571
Number of pages7
JournalOrganic Letters
Volume26
Issue number40
DOIs
StatePublished - 11 Oct 2024

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© 2024 American Chemical Society.

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