Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA.
Angew Chem Int Ed Engl. 2011 Aug 22;50(35):8127-30. doi: 10.1002/anie.201102045. Epub 2011 Jul 11.
Jack of all trades: water-soluble salts of DHF underwent self-condensation to afford the threo diastereomer of pentulosonic acid, through differing reaction pathways contingent on the metal salt used. This transformation exemplifies the diverging roles of DHF as a nucleophile (a synthon for α-hydroxyacetyl anion) and an electrophile (an α-carboxyglycolaldehyde equivalent).
DHF 的水溶性盐通过不同的反应途径进行自身缩合,得到戊糖二酸的 threo 非对映异构体,这取决于所使用的金属盐。这种转化体现了 DHF 作为亲核试剂(α-羟乙酰阴离子的前体)和亲电试剂(α-羰代乙二醇醛等价物)的不同作用。