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Chemo- and Diastereoselective Synthesis of N -Propargyl Oxazolidines through a Copper-Catalyzed Domino A 3 Reaction

2019; American Chemical Society; Volume: 84; Issue: 9 Linguagem: Inglês

10.1021/acs.joc.8b03244

1520-6904

Yazhen Zhang, Liliang Huang, Xiaoyang Li, Le Wang, Huangdi Feng,

Cyclopropane Reaction Mechanisms

Herein we describe a highly chemoselective A3-coupling/annulation of amino alcohols, formaldehyde, two kinds of aldehydes and alkynes, catalyzed by copper(II). This cascade reaction, employing readily available materials, provides a new and highly effective access to chiral N-propargyl oxazolidines with good diastereoselectivity (up to >20:1). In the case of ortho-substituted aromatic aldehydes, an intriguing steric effect is observed: a bulky group exhibits a remarkably adverse effect on the diastereoselectivity for the formation of the title molecule.