Logo image
Gold-Catalyzed Addition of β-Oxo Enols at Tethered Alkynes via a Non-Conia-ene Pathway: Observation of a Formal 1,3-Hydroxymethylidene Migration
期刊文章   同儕審查

Gold-Catalyzed Addition of β-Oxo Enols at Tethered Alkynes via a Non-Conia-ene Pathway: Observation of a Formal 1,3-Hydroxymethylidene Migration

Akshay Subhash Narode, Yeu-Shiuan Ho, Mu-Jeng ChengRai-Shung Liu
Organic Letters, 卷.25(9), 頁碼.1589-1594
03/2023
PMID: 36861973

摘要

Biochemistry Physical and Theoretical Chemistry Organic Chemistry
With the relay process of Ag(I)/Au(I) catalysts, a one-pot synthesis of skeletally rearranged (1-hydroxymethylidene)indene derivatives from 2-alkynylbenzaldehydes and α-diazo esters is described. This cascade sequence involves Au(I)-catalyzed 5-endo-dig attack of highly enolizable aldehydes at the tethered alkynes, leading to carbocyclizations with a formal 1,3-hydroxymethylidene transfer. On the basis of density functional theory calculations, the mechanism likely involves formation of cyclopropylgold carbenes, followed by an appealing 1,2-cyclopropane migration.

相關連結

指標

1 檢視次數

詳細資料

Logo image