Issue 18, 2010

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Apr 2010
Accepted
10 Jun 2010
First published
12 Jul 2010

Org. Biomol. Chem., 2010,8, 4085-4089

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

T. C. Nugent, M. N. Umar and A. Bibi, Org. Biomol. Chem., 2010, 8, 4085 DOI: 10.1039/C0OB00049C

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