A modular approach to nonracemic cyclo-BINOLs. Preparation of symmetrically and unsymmetrically substituted ligands

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7017-7020

  Lipshutz, Bruce H ^a   Shin, Young Jun ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; LIGAND; NAPHTHOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032563953     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01468-3     Document Type: Article

References (18)

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2. 2. Rosinio, C.; Franzini, L.; Raffaelli, A. Salvadori, P. Synthesis, 1992, 503.
3. 3. For examples, see Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; Cox, P.J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253 [For other examples of disubstituted BINOLs from this laboratory, see W. Wang, Ph.D. thesis, University of Waterloo, 1992]; Lingenfelter, D.S.; Helgeson, R.C.; Cram, D.J. J. Org. Chem. 1981, 46, 393.
4. 3. For examples, see Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; Cox, P.J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253 [For other examples of disubstituted BINOLs from this laboratory, see W. Wang, Ph.D. thesis, University of Waterloo, 1992]; Lingenfelter, D.S.; Helgeson, R.C.; Cram, D.J. J. Org. Chem. 1981, 46, 393.
5. 3. For examples, see Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; Cox, P.J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253 [For other examples of disubstituted BINOLs from this laboratory, see W. Wang, Ph.D. thesis, University of Waterloo, 1992]; Lingenfelter, D.S.; Helgeson, R.C.; Cram, D.J. J. Org. Chem. 1981, 46, 393.
6. 3. For examples, see Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; Cox, P.J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253 [For other examples of disubstituted BINOLs from this laboratory, see W. Wang, Ph.D. thesis, University of Waterloo, 1992]; Lingenfelter, D.S.; Helgeson, R.C.; Cram, D.J. J. Org. Chem. 1981, 46, 393.
7. 4. Lipshutz, B.H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753.
8. 5. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
9. 6. Determined by 500 MHz NMR analysis (± 2%) of the corresponding Mosher diester.
10. 7. Martinborough, E.; Denti, T. M.; Castro, P. P.; Wyman, T. B.; Knobler, C. B.; Diederich, F. Helv. Chim. Acta. 1995, 78, 1037.
11. 8. (a) See, for example, Sharp, M. J.; Chang, W.; Snieckus, V. Tetrahedron Lett. 1987, 28, 5093, and references therein;
12. (b) Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, H.; Kodama, S-I.; Nakajima, I.; Minato, A.; Kumada, M. Bull Chem. Soc. Jpn. 1976, 49, 1958.
13. 9. Hughes, D. L. Org. React. 1992, 42, 335; Mitsunobu, O. Synthesis 1981, 1.
14. 9. Hughes, D. L. Org. React. 1992, 42, 335; Mitsunobu, O. Synthesis 1981, 1.
15. 10. Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.
16. 11. Dewar, M.J.S.; Nakaya T. J. Am. Chem. Soc. 1968, 90, 7134.
17. 12. For a representative example, see Ishihara, K.; Kurihara, H. Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
18. 4. Filtration and solvent removal in vacuo afforded crude material which was purified by column chromatography (silica gel; 4:1 EtOAc: pet ether) to give a colorless solid (163 mg, 83%).