Jump to main content
Jump to site search

Issue 18, 2010
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 Apr 2010, accepted on 10 Jun 2010 and first published on 12 Jul 2010


Article type: Paper
DOI: 10.1039/C0OB00049C
Org. Biomol. Chem., 2010,8, 4085-4089

  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements