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Enantioselective syntheses of various chiral multicyclic compounds with quaternary carbon stereocenters by catalytic intramolecular cycloaddition.
J Am Chem Soc. 2008 Mar 19; 130(11):3451-7.JA

Abstract

The intramolecular cycloaddition of 1,n-diene-ynes (n = 4-6), where alkyne and alkene moieties are connected by a 1,1-disubstituted alkene, was examined using a chiral rhodium catalyst, and various types of cycloadducts with quaternary carbon stereocenter(s) were obtained in high to excellent enantiomeric excess. In the case of 1,4-diene-ynes, tricyclic, bicyclic, and spirocyclic compounds were obtained depending upon the substituents at the 2-position of the 1,4-diene moiety and those at their alkyne termini. On the other hand, 1,5- and 1,6-diene-ynes gave tricyclic and bicyclic compounds, which included medium-sized ring systems. The mechanistic considerations for different reaction pathways and the synthetic transformation of tricyclic products into functionalized spirocyclic compounds are also described. The reaction of enediynes, where two alkyne moieties are connected by a 1,1-disubstituted alkene, was also examined, and sterically strained tricyclic compounds with two carbon stereocenters were obtained.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan. tshibata@waseda.jpNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

18293972

Citation

Shibata, Takanori, et al. "Enantioselective Syntheses of Various Chiral Multicyclic Compounds With Quaternary Carbon Stereocenters By Catalytic Intramolecular Cycloaddition." Journal of the American Chemical Society, vol. 130, no. 11, 2008, pp. 3451-7.
Shibata T, Tahara YK, Tamura K, et al. Enantioselective syntheses of various chiral multicyclic compounds with quaternary carbon stereocenters by catalytic intramolecular cycloaddition. J Am Chem Soc. 2008;130(11):3451-7.
Shibata, T., Tahara, Y. K., Tamura, K., & Endo, K. (2008). Enantioselective syntheses of various chiral multicyclic compounds with quaternary carbon stereocenters by catalytic intramolecular cycloaddition. Journal of the American Chemical Society, 130(11), 3451-7. https://doi.org/10.1021/ja0762083
Shibata T, et al. Enantioselective Syntheses of Various Chiral Multicyclic Compounds With Quaternary Carbon Stereocenters By Catalytic Intramolecular Cycloaddition. J Am Chem Soc. 2008 Mar 19;130(11):3451-7. PubMed PMID: 18293972.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective syntheses of various chiral multicyclic compounds with quaternary carbon stereocenters by catalytic intramolecular cycloaddition. AU - Shibata,Takanori, AU - Tahara,Yu-ki, AU - Tamura,Kohei, AU - Endo,Kohei, Y1 - 2008/02/23/ PY - 2008/2/26/pubmed PY - 2008/4/30/medline PY - 2008/2/26/entrez SP - 3451 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 130 IS - 11 N2 - The intramolecular cycloaddition of 1,n-diene-ynes (n = 4-6), where alkyne and alkene moieties are connected by a 1,1-disubstituted alkene, was examined using a chiral rhodium catalyst, and various types of cycloadducts with quaternary carbon stereocenter(s) were obtained in high to excellent enantiomeric excess. In the case of 1,4-diene-ynes, tricyclic, bicyclic, and spirocyclic compounds were obtained depending upon the substituents at the 2-position of the 1,4-diene moiety and those at their alkyne termini. On the other hand, 1,5- and 1,6-diene-ynes gave tricyclic and bicyclic compounds, which included medium-sized ring systems. The mechanistic considerations for different reaction pathways and the synthetic transformation of tricyclic products into functionalized spirocyclic compounds are also described. The reaction of enediynes, where two alkyne moieties are connected by a 1,1-disubstituted alkene, was also examined, and sterically strained tricyclic compounds with two carbon stereocenters were obtained. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/18293972/Enantioselective_syntheses_of_various_chiral_multicyclic_compounds_with_quaternary_carbon_stereocenters_by_catalytic_intramolecular_cycloaddition_ DB - PRIME DP - Unbound Medicine ER -