Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Org Lett. 2013 Sep 6;15(17):4516-9. doi: 10.1021/ol402081p. Epub 2013 Aug 15.
An enantioselective α-hydroxyacetate aldol reaction that employs N-acetyl pyrroles as activated ester equivalents and generates syn 1,2-diols in good yield and diastereoselectivity is reported. This dinuclear zinc-ProPhenol-catalyzed transformation proceeds with high enantioselectivity with a wide variety of substrates including aryl, alyl, and alkenyl aldehydes. The resulting α,β-dihydroxy activated esters are versatile intermediates for the synthesis of a variety of carboxylic acid derivatives including amides, esters, and unsymmetrical ketones.
报道了一种对映选择性的α-羟基乙酸酯羟醛反应，该反应使用 N-乙酰基吡咯作为活化酯等价物，并以良好的收率和非对映选择性生成顺式 1,2-二醇。这种双核锌-ProPhenol 催化的转化具有高度的对映选择性，可以与各种底物（包括芳基、烯丙基和烯基醛）反应。得到的α，β-二羟基活化酯是合成各种羧酸衍生物（包括酰胺、酯和不对称酮）的多功能中间体。
