Stereoselective synthesis of 1,3,5-trienes from alkynones and allyl carbonyl compounds through C-C σ-bond cleavage under transition-metal-free conditions

Authors：Cheng, Lu; Wang, Mengdan; Yang, Yajie; Wang, Zongkang; Zhu, Yilin; Kong, Lingkai^*; Li, Yanzhong^*

Source：Organic Chemistry Frontiers, 2022, 9(12): 3354-3359.

DOI：10.1039/d2qo00617k

• CONJUGATED TRIENES
• STEREOCONTROLLED SYNTHESIS
• RING EXPANSION
• INSERTION
• ALKYNES
• CONVENIENT
• ESTERS
• OLIGOMERS
• ALCOHOLS
• ANALOGS

An atom-economical transition-metal-free protocol for the stereoselective synthesis of conjugated trienes has been developed. These transformations were realized through base promoted C-C sigma-bond cleavage reactions of allyl carbonyl compounds. This methodology efficiently constructs a broad range of conjugated trienes with the advantages of mild reaction conditions, low cost and operational simplicity.