Anti-1,2-Diols via Ni-Catalyzed Reductive Coupling of Alkynes and α-Oxyaldehydes

Organic Letters 7(14), 2937-2940, DOI: 10.1021/ol050881k

Ni-catalyzed reductive coupling of aryl alkynes (1) andenantiomerically enriched α-oxyaldehydes (2) afford differentiated anti-1,2-diols (3) with high diastereoselectivity and regioselectivity, despite the fact that the methoxymethyl (MOM) and para-methoxybenzyl (PMB) protective groups typically favor syn-1,2-diol formation in carbonyl addition reactions of this family of aldehydes."