anti-1,2-Diols via Ni-catalyzed reductive coupling of alkynes and alpha-oxyaldehydes.
[reaction: see text] Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiomerically enriched alpha-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.
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, 02139, USA.
Torsak
T
Luanphaisarnnont
Chudi O
CO
Ndubaku
Timothy F
TF
Jamison
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D000480:Alkynes; D009532:Nickel