Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes.
J Org Chem. 2007 Aug 17; 72(17):6521-5.JO

Abstract

The enantioselective intramolecular [2 + 2 + 2] cycloaddition of various enediynes, where two acetylenic moieties are connected by a trans-olefinic moiety, gave chiral tricyclic cyclohexa-1,3-dienes using Rh-H8-BINAP catalyst. In the case of carbon-atom-tethered enediynes, enantioselectivity was generally good-to-high regardless of the substituents on their alkyne termini. In contrast, with heteroatom-tethered enediynes, appropriate substituents were required to induce the oxidative coupling of alkyne and alkene moieties before that of two alkyne moieties, which would be important for highly enantioselective intramolecular cycloaddition.

Authors+Show Affiliations

Shibata T

Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan. tshibata@waseda.jp

Kurokawa H

No affiliation info available

Kanda K

No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17636959

Citation

Shibata, Takanori, et al. "Enantioselective Intramolecular [2 + 2 + 2] Cycloaddition of Enediynes for the Synthesis of Chiral Cyclohexa-1,3-dienes." The Journal of Organic Chemistry, vol. 72, no. 17, 2007, pp. 6521-5.

Shibata T, Kurokawa H, Kanda K. Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes. J Org Chem. 2007;72(17):6521-5.

Shibata, T., Kurokawa, H., & Kanda, K. (2007). Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes. The Journal of Organic Chemistry, 72(17), 6521-5.

Shibata T, Kurokawa H, Kanda K. Enantioselective Intramolecular [2 + 2 + 2] Cycloaddition of Enediynes for the Synthesis of Chiral Cyclohexa-1,3-dienes. J Org Chem. 2007 Aug 17;72(17):6521-5. PubMed PMID: 17636959.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes. AU - Shibata,Takanori, AU - Kurokawa,Hiroshi, AU - Kanda,Kazumasa, Y1 - 2007/07/18/ PY - 2007/7/20/pubmed PY - 2007/7/20/medline PY - 2007/7/20/entrez SP - 6521 EP - 5 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 17 N2 - The enantioselective intramolecular [2 + 2 + 2] cycloaddition of various enediynes, where two acetylenic moieties are connected by a trans-olefinic moiety, gave chiral tricyclic cyclohexa-1,3-dienes using Rh-H8-BINAP catalyst. In the case of carbon-atom-tethered enediynes, enantioselectivity was generally good-to-high regardless of the substituents on their alkyne termini. In contrast, with heteroatom-tethered enediynes, appropriate substituents were required to induce the oxidative coupling of alkyne and alkene moieties before that of two alkyne moieties, which would be important for highly enantioselective intramolecular cycloaddition. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17636959/Enantioselective_intramolecular_[2_+_2_+_2]_cycloaddition_of_enediynes_for_the_synthesis_of_chiral_cyclohexa_13_dienes_ L2 - https://doi.org/10.1021/jo070762d DB - PRIME DP - Unbound Medicine ER -

Tags

Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes.J Org Chem. 2007 Aug 17; 72(17):6521-5.JO