Synthesis and resolution of a new chiral C2-symmetric bisphenol: Trans-1,2-bis(2-hydroxyphenyl)cyclopentane

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2589-2592

  Whitesell, James K ^a   Apodaca, Richard ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS(2 HYDROXYPHENYL)CYCLOPENTANE; LIGAND; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0030958214     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00421-8     Document Type: Article

References (21)

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2. Yamamoto, H.; Kobayashi, S.; Kanemasa, S. Tetrahedron: Asymmetry 1996, 7, 149.
3. 2-symmetric catechol, see: Kelly, T.R.; Chandrakumar, N.S.; Saha, J.K. J. Org. Chem. 1989, 54, 980.
4. Whitesell, J.K. Chem. Rev. 1989, 89, 1581.
5. For a biaryl-based approach, see: Bao, J.; Wulff, W.D. Dominy, J.B.; Fumo, M.J.; Grant, E.B.; Rob, A.C.; Whitcomb, M.C.; Yeung, S.-M.; Ostrander, R.L.; Rheingold, A.L. J. Am. Chem. Soc. 1996, 118, 3392.
6. Properly positioned aryl groups are thought to play key roles in a variety of chiral recognition phenomena. For a review, see: Jones, G.B.; Chapman, B.J. Synthesis 1995, 475.
7. To our knowledge, the only other bis(hydroxyphenyl)cyclopentane ever reported is the 4-hydroxyphenyl analog of 2: (a) Meuller, G.P.; Fleckenstein, J.G.; Tallent, W.H. J. Am. Chem. Soc. 1951, 73, 2651. For a related coumarin dimer-derived cyclobutane, see:
8. (b) Saigo, K.; Sekimoto, K.; Yonezawa, N.; Ishi, F.; Hasegawa, M. Bull. Chem. Soc. Jpn. 1985, 58, 1006. The diphenylphosphino analog of 2 has been prepared in enantiopure form:
9. (c) Fukada, N.; Mashima, K.; Matsumura, Y.; Takaya, H. Tetrahedron Lett. 1990, 31, 7185.
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12. 4. Solvent was removed in vacua and the oily residue was pumped under vacuum (0.05 mm Hg, rt) overnight, yielding an orange solid / oil mixture which was triturated with hot Skelly B (2×50 mL). Evaporation of the solution followed by crystallization of the resulting residue from Skelly B yielded cyclopentene 7 as yellow prisms (2.58 g, 57%): mp 76-77 °C.
13. Kursanov, D.N.; Parnes, Z.N.; Loim, N.M. Synthesis 1974, 633.
14. 13C NMR signal for 9 relative to 8 (2.1 ppm) agrees with an empirical rule that predicts a ca. 2.5 ppm downfield shift for every anti vicinal hydrogen-hydrogen interaction:
15. (b) Whitesell, J.K.; Minton, M.A. J. Am. Chem. Soc. 1987, 709, 225.
16. Curtin, D.Y.; Bender, P.E.; Hetzer, D.S. J. Org. Chem. 1971, 36, 565.
17. 1H NMR spectra of the crude reaction product. An additional product was also present (ca. 10%). This impurity may result from monodemethylation during the basic isomerization conditions.
18. McOmie, J.F.W.; Watts, M.L.; West, D.E. Tetrahedron 1968, 24, 2289.
19. See reference 2 and: Trost, B.M.; Belletire, J.L.; Godleski, S.; McDougal, P.G.; Balkovec, J.M.; Baldwin, J.J.; Christy, M.E.; Ponticello, G.S.; Varga, S.L.; Springer, J.P. J. Org. Chem. 1986, 57, 2370.
20. We thank Dr. Vincent Lynch for this analysis. Details will be published elsewhere.
21. Whitesell, J.K.; Reynolds, D. J. Org. Chem. 1983, 48, 3548.