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Formation of disubstituted beta-lactones using bifunctional catalysis.
Org Lett. 2005 Apr 28; 7(9):1809-12.OL

Abstract

[reaction: see text] Acid chlorides and aromatic aldehydes react in the presence of a stoichiometric amount of a tertiary amine and catalytic amounts of a cinchona alkaloid derivative and a Lewis acid to produce beta-lactones in high diastereo- and enantioselectivity. The sense of the diastereoselectivity depends on the substitution of the acid chloride, with the reactions of aliphatic acid chlorides giving predominantly the trans-isomer and those of alkoxyacetyl chlorides favoring formation of the cis-isomer.

Authors+Show Affiliations

Calter MA
Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459-0180, USA. mcalter@wesleyan.edu
Tretyak OA
No affiliation info available
Flaschenriem C
No affiliation info available

MeSH

CatalysisCinchona AlkaloidsLactonesMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15844912

Citation

Calter, Michael A., et al. "Formation of Disubstituted Beta-lactones Using Bifunctional Catalysis." Organic Letters, vol. 7, no. 9, 2005, pp. 1809-12.
Calter MA, Tretyak OA, Flaschenriem C. Formation of disubstituted beta-lactones using bifunctional catalysis. Org Lett. 2005;7(9):1809-12.
Calter, M. A., Tretyak, O. A., & Flaschenriem, C. (2005). Formation of disubstituted beta-lactones using bifunctional catalysis. Organic Letters, 7(9), 1809-12.
Calter MA, Tretyak OA, Flaschenriem C. Formation of Disubstituted Beta-lactones Using Bifunctional Catalysis. Org Lett. 2005 Apr 28;7(9):1809-12. PubMed PMID: 15844912.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Formation of disubstituted beta-lactones using bifunctional catalysis. AU - Calter,Michael A, AU - Tretyak,Olexandr A, AU - Flaschenriem,Christine, PY - 2005/4/23/pubmed PY - 2006/2/10/medline PY - 2005/4/23/entrez SP - 1809 EP - 12 JF - Organic letters JO - Org Lett VL - 7 IS - 9 N2 - [reaction: see text] Acid chlorides and aromatic aldehydes react in the presence of a stoichiometric amount of a tertiary amine and catalytic amounts of a cinchona alkaloid derivative and a Lewis acid to produce beta-lactones in high diastereo- and enantioselectivity. The sense of the diastereoselectivity depends on the substitution of the acid chloride, with the reactions of aliphatic acid chlorides giving predominantly the trans-isomer and those of alkoxyacetyl chlorides favoring formation of the cis-isomer. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15844912/Formation_of_disubstituted_beta_lactones_using_bifunctional_catalysis_ DB - PRIME DP - Unbound Medicine ER -