Journal of Organic Chemistry p. 14385 - 14395 (2018)
Update date:2022-08-03
Topics:
Lu, Lin
Chen, Chuwei
Jiang, Huanfeng
Yin, Biaolin
A protocol for three-component reactions of cyclic ethers, α-diazo esters, and weak nitrogen, oxygen, carbon, and sulfur nucleophiles (pKa = 2.2-14.8) to afford a variety of structurally complex α-oxyalkylated esters is reported. These reactions involve intermolecular activation of the cyclic ether (present in excess) by the α-diazo ester to form an oxonium ylide under metal-free conditions, followed by ring opening by the nucleophile.
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