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Role of pseudoephedrine as chiral auxiliary in the "acetate-type" aldol reaction with chiral aldehydes; asymmetric synthesis of highly functionalized chiral building blocks.
J Org Chem. 2011 Jan 21; 76(2):460-70.JO

Abstract

We have studied in depth the aldol reaction between acetamide enolates and chiral α-heterosubstituted aldehydes using pseudoephedrine as chiral auxiliary under double stereodifferentiation conditions, showing that high diastereoselectivities can only be achieved under the matched combination of reagents and provided that the α-heteroatom-containing substituent of the chiral aldehyde is conveniently protected. Moreover, the obtained highly functionalized aldols have been employed as very useful starting materials for the stereocontrolled preparation of other interesting compounds and chiral building blocks such as pyrrolidines, indolizidines, and densely functionalized β-hydroxy and β-amino ketones using simple and high-yielding methodologies.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ocejo M
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, P.O. Box 644, E-48080 Bilbao, Spain.
Carrillo L
No affiliation info available
Vicario JL
No affiliation info available
Badía D
No affiliation info available
Reyes E
No affiliation info available

MeSH

AcetatesAldehydesIndicators and ReagentsKetonesMagnetic Resonance SpectroscopyMolecular StructurePseudoephedrinePyrrolidinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21188970

Citation

Ocejo, Marta, et al. "Role of Pseudoephedrine as Chiral Auxiliary in the "acetate-type" Aldol Reaction With Chiral Aldehydes; Asymmetric Synthesis of Highly Functionalized Chiral Building Blocks." The Journal of Organic Chemistry, vol. 76, no. 2, 2011, pp. 460-70.
Ocejo M, Carrillo L, Vicario JL, et al. Role of pseudoephedrine as chiral auxiliary in the "acetate-type" aldol reaction with chiral aldehydes; asymmetric synthesis of highly functionalized chiral building blocks. J Org Chem. 2011;76(2):460-70.
Ocejo, M., Carrillo, L., Vicario, J. L., Badía, D., & Reyes, E. (2011). Role of pseudoephedrine as chiral auxiliary in the "acetate-type" aldol reaction with chiral aldehydes; asymmetric synthesis of highly functionalized chiral building blocks. The Journal of Organic Chemistry, 76(2), 460-70. https://doi.org/10.1021/jo101878j
Ocejo M, et al. Role of Pseudoephedrine as Chiral Auxiliary in the "acetate-type" Aldol Reaction With Chiral Aldehydes; Asymmetric Synthesis of Highly Functionalized Chiral Building Blocks. J Org Chem. 2011 Jan 21;76(2):460-70. PubMed PMID: 21188970.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Role of pseudoephedrine as chiral auxiliary in the "acetate-type" aldol reaction with chiral aldehydes; asymmetric synthesis of highly functionalized chiral building blocks. AU - Ocejo,Marta, AU - Carrillo,Luisa, AU - Vicario,Jose L, AU - Badía,Dolores, AU - Reyes,Efraim, Y1 - 2010/12/28/ PY - 2010/12/30/entrez PY - 2010/12/30/pubmed PY - 2011/5/20/medline SP - 460 EP - 70 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 2 N2 - We have studied in depth the aldol reaction between acetamide enolates and chiral α-heterosubstituted aldehydes using pseudoephedrine as chiral auxiliary under double stereodifferentiation conditions, showing that high diastereoselectivities can only be achieved under the matched combination of reagents and provided that the α-heteroatom-containing substituent of the chiral aldehyde is conveniently protected. Moreover, the obtained highly functionalized aldols have been employed as very useful starting materials for the stereocontrolled preparation of other interesting compounds and chiral building blocks such as pyrrolidines, indolizidines, and densely functionalized β-hydroxy and β-amino ketones using simple and high-yielding methodologies. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21188970/Role_of_pseudoephedrine_as_chiral_auxiliary_in_the_"acetate_type"_aldol_reaction_with_chiral_aldehydes L2 - https://doi.org/10.1021/jo101878j DB - PRIME DP - Unbound Medicine ER -