Rapid atropisomerization of 1,1′:5′,1″-ternaphthalene-2,2′,6′,2″-tetrol (TERNOL) and its inhibition by tethering at positions 7 and 7″

Tetrahedron

Volumn 63, Issue 8, 2007, Pages 1762-1769

  Sugimura, Takashi ^a   Matsushita, Naohiro ^a   Minokami, Keiko ^a   Kurita, Shinya ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

Atropisomerization; Axial chirality; Bidentate ligand; Metathesis

Indexed keywords

1,1':5',1'' TERNAPHTHALENE 2,2',6',2'' TETROL; ANION; NAPHTHALENE DERIVATIVE; OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ISOMERIZATION; MOLECULAR DYNAMICS; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 33846203906     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.046     Document Type: Article

References (16)

1. For a recent review of BINOL, see:. Brunel J.M. Chem. Rev. 105 (2005) 857
2. For a higher analog of TERNOL, see:. Sugimura T., Kurita S., Inoue S., Fujita M., Okuyama T., and Tai A. Enantiomer 6 (2001) 35
3. For other higher analogs of 2,3-naphthodiol connected at 1,4-poisons, see:. Fuji K., Furuta T., and Tanaka K. Org. Lett. 3 (2001) 169 (correction 961)
4. Belohradsky M., Budesinsky M., Gunterova J., Hodacova J., Holy P., Zavada J., Cisarova I., and Podlaha J. J. Org. Chem. 61 (1996) 1205
5. Sugimura T., Inoue S., and Tai A. Tetrahedron Lett. 39 (1998) 6487
6. Sugimura T., Wada M., and Tai A. Enantiomer 5 (2000) 23
7. Belohradsky M., Budesinsky M., Hodacova J., Holy P., Zavada J., Cisarova I., and Podlaha J. Tetrahedron 52 (1996) 11013
8. For a recent computational study for the isomerization mechanism of BINOL, see:. Meca L., Reha D., and Havlas Z. J. Org. Chem. 68 (2003) 5677
9. For general reviews, see:. Grubbs R.H., and Trnka T.M. In: Murahashi S.-I. (Ed). Ruthenium in Organic Synthesis (2004), Wiley-VCH, Weinheim 153-177
10. Schmidt B., and Hermanns J. In: Dötz K.H. (Ed). Metal Carbenes in Organic Synthesis (2004), Springer, Berlin 223-267
11. Lee C.W., and Grubbs R.H. Org. Lett. 2 (2000) 2145
12. Blechert S., and Connon S.J. Angew. Chem., Int. Ed. 42 (2003) 1900
13. Prunet J. Angew. Chem., Int. Ed. 42 (2003) 2826
14. Deussen H.J., Hendrickx E., Boutton C., Krog D., Clays K., Bechgaard K., Persoons A., and Bjornholm T. J. Am. Chem. Soc. 118 (1996) 6841
15. Thirsk C., Hawkes G.E., Kroemer R.T., Liedl K.R., Loerting T., and Thomas N.R. J. Chem. Soc., Perkin Trans. 2 (2002) 1510
16. Aoki Y., Sakaguchi S., and Ishii Y. Adv. Synth. Catal. 346 (2004) 199