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Organocatalytic asymmetric assembly reactions: one-pot synthesis of functionalized beta-amino alcohols from aldehydes, ketones, and azodicarboxylates.
Org Lett. 2003 May 15; 5(10):1685-8.OL

Abstract

[reaction: see text] l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active beta-amino alcohols. This assembly reaction uses both aldehydes and ketones as donors in one pot. The aldol-derived stereocenter is formed with a reduced facial selectivity in reactions involving (R)-amino aldehydes. The reactions can be performed on a multigram scale under operationally simple and safe conditions without the requirement of an inert atmosphere or dry solvents.

Authors+Show Affiliations

Chowdari NS
The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Ramachary DB
No affiliation info available
Barbas CF
No affiliation info available

MeSH

AldehydesAmino AlcoholsAza CompoundsCatalysisDicarboxylic AcidsKetonesModels, MolecularMolecular ConformationProlineSolventsStereoisomerism

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12735752

Citation

Chowdari, Naidu S., et al. "Organocatalytic Asymmetric Assembly Reactions: One-pot Synthesis of Functionalized Beta-amino Alcohols From Aldehydes, Ketones, and Azodicarboxylates." Organic Letters, vol. 5, no. 10, 2003, pp. 1685-8.
Chowdari NS, Ramachary DB, Barbas CF. Organocatalytic asymmetric assembly reactions: one-pot synthesis of functionalized beta-amino alcohols from aldehydes, ketones, and azodicarboxylates. Org Lett. 2003;5(10):1685-8.
Chowdari, N. S., Ramachary, D. B., & Barbas, C. F. (2003). Organocatalytic asymmetric assembly reactions: one-pot synthesis of functionalized beta-amino alcohols from aldehydes, ketones, and azodicarboxylates. Organic Letters, 5(10), 1685-8.
Chowdari NS, Ramachary DB, Barbas CF. Organocatalytic Asymmetric Assembly Reactions: One-pot Synthesis of Functionalized Beta-amino Alcohols From Aldehydes, Ketones, and Azodicarboxylates. Org Lett. 2003 May 15;5(10):1685-8. PubMed PMID: 12735752.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic asymmetric assembly reactions: one-pot synthesis of functionalized beta-amino alcohols from aldehydes, ketones, and azodicarboxylates. AU - Chowdari,Naidu S, AU - Ramachary,D B, AU - Barbas,Carlos F,3rd PY - 2003/5/9/pubmed PY - 2003/8/26/medline PY - 2003/5/9/entrez SP - 1685 EP - 8 JF - Organic letters JO - Org Lett VL - 5 IS - 10 N2 - [reaction: see text] l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active beta-amino alcohols. This assembly reaction uses both aldehydes and ketones as donors in one pot. The aldol-derived stereocenter is formed with a reduced facial selectivity in reactions involving (R)-amino aldehydes. The reactions can be performed on a multigram scale under operationally simple and safe conditions without the requirement of an inert atmosphere or dry solvents. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/12735752/Organocatalytic_asymmetric_assembly_reactions:_one_pot_synthesis_of_functionalized_beta_amino_alcohols_from_aldehydes_ketones_and_azodicarboxylates_ DB - PRIME DP - Unbound Medicine ER -