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Asymmetric syn-selective direct aldol reaction of protected hydroxyacetone catalyzed by primary amino acid derived bifunctional organocatalyst in the presence of water.
Org Biomol Chem. 2011 Apr 21; 9(8):2731-42.OB

Abstract

A new series of water compatible primary-tertiary diamine catalysts derived from natural primary amino acids bearing a hydrophobic side chain have been synthesized. These new primary-tertiary diamine-Brønsted acid conjugates bifunctional organocatalysts efficiently catalyzes the asymmetric direct syn selective cross-aldol reaction of different protected hydroxyacetone with various aldehydes in high yield (94%) and high enantioselectivity (up to 97% ee of syn) and dr of 91 : 9 (syn/anti) under mild reaction conditions.

Authors+Show Affiliations

Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar-143005, India.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21359299

Citation

Kumar, Akshay, et al. "Asymmetric Syn-selective Direct Aldol Reaction of Protected Hydroxyacetone Catalyzed By Primary Amino Acid Derived Bifunctional Organocatalyst in the Presence of Water." Organic & Biomolecular Chemistry, vol. 9, no. 8, 2011, pp. 2731-42.
Kumar A, Singh S, Kumar V, et al. Asymmetric syn-selective direct aldol reaction of protected hydroxyacetone catalyzed by primary amino acid derived bifunctional organocatalyst in the presence of water. Org Biomol Chem. 2011;9(8):2731-42.
Kumar, A., Singh, S., Kumar, V., & Chimni, S. S. (2011). Asymmetric syn-selective direct aldol reaction of protected hydroxyacetone catalyzed by primary amino acid derived bifunctional organocatalyst in the presence of water. Organic & Biomolecular Chemistry, 9(8), 2731-42. https://doi.org/10.1039/c0ob00898b
Kumar A, et al. Asymmetric Syn-selective Direct Aldol Reaction of Protected Hydroxyacetone Catalyzed By Primary Amino Acid Derived Bifunctional Organocatalyst in the Presence of Water. Org Biomol Chem. 2011 Apr 21;9(8):2731-42. PubMed PMID: 21359299.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric syn-selective direct aldol reaction of protected hydroxyacetone catalyzed by primary amino acid derived bifunctional organocatalyst in the presence of water. AU - Kumar,Akshay, AU - Singh,Sarbjit, AU - Kumar,Vikas, AU - Chimni,Swapandeep Singh, Y1 - 2011/02/25/ PY - 2011/3/2/entrez PY - 2011/3/2/pubmed PY - 2011/7/22/medline SP - 2731 EP - 42 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 9 IS - 8 N2 - A new series of water compatible primary-tertiary diamine catalysts derived from natural primary amino acids bearing a hydrophobic side chain have been synthesized. These new primary-tertiary diamine-Brønsted acid conjugates bifunctional organocatalysts efficiently catalyzes the asymmetric direct syn selective cross-aldol reaction of different protected hydroxyacetone with various aldehydes in high yield (94%) and high enantioselectivity (up to 97% ee of syn) and dr of 91 : 9 (syn/anti) under mild reaction conditions. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/21359299/Asymmetric_syn_selective_direct_aldol_reaction_of_protected_hydroxyacetone_catalyzed_by_primary_amino_acid_derived_bifunctional_organocatalyst_in_the_presence_of_water_ L2 - https://doi.org/10.1039/c0ob00898b DB - PRIME DP - Unbound Medicine ER -