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exo- and enantioselective cycloaddition of azomethine ylides generated from N-alkylidene glycine esters using chiral phosphine-copper complexes.
Org Lett. 2003 Dec 25; 5(26):5043-6.OL

Abstract

High diastereo- and enantioselectivities were obtained for the asymmetric 1,3-dipolar cycloaddition of azomethine ylides generated from N-alkylideneglycine esters with dipolarophiles using chiral phosphine-copper complexes as catalysts. Whereas the cycloaddition of azomethine ylides catalyzed by metal salts generally afforded endo-adducts as the predominant product, the present method is the first example of an exo-selective cycloaddition. [reaction: see text]

Authors+Show Affiliations

Oderaotoshi Y
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.
Cheng W
No affiliation info available
Fujitomi S
No affiliation info available
Kasano Y
No affiliation info available
Minakata S
No affiliation info available
Komatsu M
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

14682760

Citation

Oderaotoshi, Yoji, et al. "Exo- and Enantioselective Cycloaddition of Azomethine Ylides Generated From N-alkylidene Glycine Esters Using Chiral Phosphine-copper Complexes." Organic Letters, vol. 5, no. 26, 2003, pp. 5043-6.
Oderaotoshi Y, Cheng W, Fujitomi S, et al. Exo- and enantioselective cycloaddition of azomethine ylides generated from N-alkylidene glycine esters using chiral phosphine-copper complexes. Org Lett. 2003;5(26):5043-6.
Oderaotoshi, Y., Cheng, W., Fujitomi, S., Kasano, Y., Minakata, S., & Komatsu, M. (2003). Exo- and enantioselective cycloaddition of azomethine ylides generated from N-alkylidene glycine esters using chiral phosphine-copper complexes. Organic Letters, 5(26), 5043-6.
Oderaotoshi Y, et al. Exo- and Enantioselective Cycloaddition of Azomethine Ylides Generated From N-alkylidene Glycine Esters Using Chiral Phosphine-copper Complexes. Org Lett. 2003 Dec 25;5(26):5043-6. PubMed PMID: 14682760.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - exo- and enantioselective cycloaddition of azomethine ylides generated from N-alkylidene glycine esters using chiral phosphine-copper complexes. AU - Oderaotoshi,Yoji, AU - Cheng,Wenji, AU - Fujitomi,Shintaro, AU - Kasano,Yukihiro, AU - Minakata,Satoshi, AU - Komatsu,Mitsuo, PY - 2003/12/20/pubmed PY - 2003/12/20/medline PY - 2003/12/20/entrez SP - 5043 EP - 6 JF - Organic letters JO - Org Lett VL - 5 IS - 26 N2 - High diastereo- and enantioselectivities were obtained for the asymmetric 1,3-dipolar cycloaddition of azomethine ylides generated from N-alkylideneglycine esters with dipolarophiles using chiral phosphine-copper complexes as catalysts. Whereas the cycloaddition of azomethine ylides catalyzed by metal salts generally afforded endo-adducts as the predominant product, the present method is the first example of an exo-selective cycloaddition. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/14682760/exo__and_enantioselective_cycloaddition_of_azomethine_ylides_generated_from_N_alkylidene_glycine_esters_using_chiral_phosphine_copper_complexes_ DB - PRIME DP - Unbound Medicine ER -