Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions

Organic & Biomolecular Chemistry
Thomas C NugentAhtaram Bibi

Abstract

A pyridine based 1,2-diamine containing only one stereogenic center has been identified for fast aldol reactions (16-48 h). Using 2-5 mol% of (R)- or (S)-PicAm-2, cyclohexanone (3.3 equiv) readily undergoes aldol reactions with o-, m-, and p-substituted aromatic aldehyde partners (limiting reagent), including the poor electrophile 4-methylbenzaldehyde (95-99% ee). Furthermore, functionalized cyclic ketone substrates have been converted into four aldol products 9-12 using the lowest catalyst loading (5.0 mol%) to date with the highest yield and enantioselectivity.

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Citations

Mar 14, 2012·Acta Crystallographica. Section E, Structure Reports Online·Muhammad Naveed UmarSeik Weng Ng
May 31, 2018·Chemical Society Reviews·Yasuhiro YamashitaShū Kobayashi
Oct 30, 2012·Organic & Biomolecular Chemistry·Thomas C NugentFoad N Tehrani
Oct 24, 2013·Chemical Society Reviews·Jacek Mlynarski, Sebastian Baś

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