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Lewis acid-promoted cyclization of heteroatom-substituted enynes.
Org Biomol Chem. 2004 Jan 21; 2(2):257-64.OB

Abstract

Lewis acid-promoted cyclizations of heteroatom-substituted enynes have been examined. The reaction of enynes and bearing silicon substituents on an alkyne afforded the halogenated five-membered gamma-lactones and gamma-lactams as the main products. The reaction of substrates and having 2-phosphonoacrylate instead of malonate also gave halogenated five-membered cyclic compounds and as the major products. The cyclized products are highly substituted and potentially useful for further synthetic transformations.

Authors+Show Affiliations

Yamazaki S
Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan. yamazaks@nara-edu.ac.jp
Yamada K
No affiliation info available
Yamamoto K
No affiliation info available

MeSH

AlkynesCarboxylic AcidsCyclizationLactamsLactones

Pub Type(s)

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

Language

eng

PubMed ID

14737650

Citation

Yamazaki, Shoko, et al. "Lewis Acid-promoted Cyclization of Heteroatom-substituted Enynes." Organic & Biomolecular Chemistry, vol. 2, no. 2, 2004, pp. 257-64.
Yamazaki S, Yamada K, Yamamoto K. Lewis acid-promoted cyclization of heteroatom-substituted enynes. Org Biomol Chem. 2004;2(2):257-64.
Yamazaki, S., Yamada, K., & Yamamoto, K. (2004). Lewis acid-promoted cyclization of heteroatom-substituted enynes. Organic & Biomolecular Chemistry, 2(2), 257-64.
Yamazaki S, Yamada K, Yamamoto K. Lewis Acid-promoted Cyclization of Heteroatom-substituted Enynes. Org Biomol Chem. 2004 Jan 21;2(2):257-64. PubMed PMID: 14737650.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lewis acid-promoted cyclization of heteroatom-substituted enynes. AU - Yamazaki,Shoko, AU - Yamada,Kuriko, AU - Yamamoto,Kagetoshi, Y1 - 2003/12/08/ PY - 2004/1/23/pubmed PY - 2004/4/2/medline PY - 2004/1/23/entrez SP - 257 EP - 64 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 2 IS - 2 N2 - Lewis acid-promoted cyclizations of heteroatom-substituted enynes have been examined. The reaction of enynes and bearing silicon substituents on an alkyne afforded the halogenated five-membered gamma-lactones and gamma-lactams as the main products. The reaction of substrates and having 2-phosphonoacrylate instead of malonate also gave halogenated five-membered cyclic compounds and as the major products. The cyclized products are highly substituted and potentially useful for further synthetic transformations. SN - 1477-0520 UR - https://www.unboundmedicine.com/medline/citation/14737650/Lewis_acid_promoted_cyclization_of_heteroatom_substituted_enynes_ DB - PRIME DP - Unbound Medicine ER -