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NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-06-30 , DOI: 10.3762/bjoc.16.129
Alyn T Davies 1 , Mark D Greenhalgh 1 , Alexandra M Z Slawin 1 , Andrew D Smith 1
Affiliation  

The N-heterocyclic carbene (NHC)-catalyzed formal [2 + 2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring opening with an amine or a reducing agent is described. The resulting β-trifluoromethyl-β-hydroxyamide and alcohol products are produced with reasonable diastereocontrol (typically ≈70:30 dr) and excellent enantioselectivity, and they can be isolated in moderate to good yield as a single diastereoisomer.

中文翻译:

NHC催化的β-三氟甲基-β-羟酰胺的对映选择性合成。

描述了在α-芳酰氧基醛和三氟苯乙酮之间进行N-杂环卡宾(NHC)催化的甲醛[2 + 2]环加成反应,然后用胺或还原剂进行开环。生成的β-三氟甲基-β-羟基酰胺和醇产物具有合理的非对映异构控制(通常≈70:30 dr)和出色的对映选择性,可以作为单一非对映异构体以中等至良好的收率分离。
更新日期:2020-06-30
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