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Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions.
Org Biomol Chem. 2010 Sep 21; 8(18):4085-9.OB

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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Authors+Show Affiliations

Nugent TC
Department of Chemistry, School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, 28759 Bremen, Germany. t.nugent@jacobs-university.de
Umar MN
No affiliation info available
Bibi A
No affiliation info available

MeSH

AlcoholsAldehydesCatalysisDiaminesKetonesMolecular StructurePicolinesStereoisomerismWater

Pub Type(s)

Journal Article

Language

eng

PubMed ID

20623075

Citation

Nugent, Thomas C., et al. "Picolylamine as an Organocatalyst Template for Highly Diastereo- and Enantioselective Aqueous Aldol Reactions." Organic & Biomolecular Chemistry, vol. 8, no. 18, 2010, pp. 4085-9.
Nugent TC, Umar MN, Bibi A. Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions. Org Biomol Chem. 2010;8(18):4085-9.
Nugent, T. C., Umar, M. N., & Bibi, A. (2010). Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions. Organic & Biomolecular Chemistry, 8(18), 4085-9. https://doi.org/10.1039/c0ob00049c
Nugent TC, Umar MN, Bibi A. Picolylamine as an Organocatalyst Template for Highly Diastereo- and Enantioselective Aqueous Aldol Reactions. Org Biomol Chem. 2010 Sep 21;8(18):4085-9. PubMed PMID: 20623075.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions. AU - Nugent,Thomas C, AU - Umar,M Naveed, AU - Bibi,Ahtaram, Y1 - 2010/07/12/ PY - 2010/7/13/entrez PY - 2010/7/14/pubmed PY - 2010/12/14/medline SP - 4085 EP - 9 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 8 IS - 18 N2 - 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. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/20623075/Picolylamine_as_an_organocatalyst_template_for_highly_diastereo__and_enantioselective_aqueous_aldol_reactions_ L2 - https://doi.org/10.1039/c0ob00049c DB - PRIME DP - Unbound Medicine ER -