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Novel lactonization of ethenetricarboxylate derivatives: intermolecular trapping of alkenes.
Org Lett. 2005 Mar 03; 7(5):759-62.OL

Abstract

A novel cyclization of 1,1-diethyl 2-tert-butyl ethenetricarboxylate (1a) in the presence of a Lewis acid afforded a 5,5-dimethyl-gamma-lactone derivative 2a. The reaction process has been shown to arise from formation by trapping of isobutylene generated in situ. Lewis acid-promoted intermolecular reactions of 1,1-diethyl 2-hydrogen ethenetricarboxylate (5) and various alkenes to afford highly functionalized gamma-lactones were also developed. [reaction: see text]

Authors+Show Affiliations

Yamazaki S
Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan. yamazaks@nara-edu.ac.jp
Ohmitsu K
No affiliation info available
Ohi K
No affiliation info available
Otsubo T
No affiliation info available
Moriyama K
No affiliation info available

MeSH

AlkenesCarboxylic AcidsCatalysisCyclizationIndicators and ReagentsLactonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15727434

Citation

Yamazaki, Shoko, et al. "Novel Lactonization of Ethenetricarboxylate Derivatives: Intermolecular Trapping of Alkenes." Organic Letters, vol. 7, no. 5, 2005, pp. 759-62.
Yamazaki S, Ohmitsu K, Ohi K, et al. Novel lactonization of ethenetricarboxylate derivatives: intermolecular trapping of alkenes. Org Lett. 2005;7(5):759-62.
Yamazaki, S., Ohmitsu, K., Ohi, K., Otsubo, T., & Moriyama, K. (2005). Novel lactonization of ethenetricarboxylate derivatives: intermolecular trapping of alkenes. Organic Letters, 7(5), 759-62.
Yamazaki S, et al. Novel Lactonization of Ethenetricarboxylate Derivatives: Intermolecular Trapping of Alkenes. Org Lett. 2005 Mar 3;7(5):759-62. PubMed PMID: 15727434.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Novel lactonization of ethenetricarboxylate derivatives: intermolecular trapping of alkenes. AU - Yamazaki,Shoko, AU - Ohmitsu,Kanae, AU - Ohi,Kunihiro, AU - Otsubo,Tetsuya, AU - Moriyama,Kayo, PY - 2005/2/25/pubmed PY - 2005/12/13/medline PY - 2005/2/25/entrez SP - 759 EP - 62 JF - Organic letters JO - Org Lett VL - 7 IS - 5 N2 - A novel cyclization of 1,1-diethyl 2-tert-butyl ethenetricarboxylate (1a) in the presence of a Lewis acid afforded a 5,5-dimethyl-gamma-lactone derivative 2a. The reaction process has been shown to arise from formation by trapping of isobutylene generated in situ. Lewis acid-promoted intermolecular reactions of 1,1-diethyl 2-hydrogen ethenetricarboxylate (5) and various alkenes to afford highly functionalized gamma-lactones were also developed. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15727434/Novel_lactonization_of_ethenetricarboxylate_derivatives:_intermolecular_trapping_of_alkenes_ DB - PRIME DP - Unbound Medicine ER -