Department of Chemistry, Brooklyn College and the City University of New York, 2900 Bedford Avenue, Brooklyn, New York 11210, USA.
Org Lett. 2010 Aug 6;12(15):3356-9. doi: 10.1021/ol101167z.
Chiral beta-fluoroamines are increasingly prevalent in medicinal compounds, but there are few efficient methods to access them from achiral starting materials. To address this, a multicomponent organocascade reaction was developed in which chiral alpha-fluoro-beta-amino aldehydes were generated in a single flask from achiral alpha,beta-unsaturated aldehydes (2), using catalyst 12a. Conversions up to 85%, dr's up to 98:2 and ee's up to 99% of the corresponding alcohol (9) were achieved in this reaction.
手性β-氟胺在药用化合物中越来越普遍，但从非手性起始原料中获得它们的方法很少。为了解决这个问题，开发了一种多组分有机级联反应，其中使用催化剂 12a，从非手性α，β-不饱和醛（2）在一个烧瓶中生成手性α-氟-β-氨基醛。在该反应中，转化率高达 85%，dr 高达 98:2，ee 高达 99%的相应醇（9）。
