1,1′-Binaphthyl-2,2′-diyl phosphoroselenoyl chloride as a chiral molecular tool for the preparation of enantiomerically pure alcohols and amines

Journal of the American Chemical Society

Volumn 128, Issue 14, 2006, Pages 4584-4585

  Murai, Toshiaki ^a   Matsuoka, Daichi ^a   Morishita, Ken ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL 2,2' DIYL PHOSPHOROSELENOYL CHLORIDE; ALCOHOL; AMINE; CHLORIDE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ASYMMETRIC CATALYSIS; CRYSTALLIZATION; ENANTIOMER; SYNTHESIS;

EID: 33646106796     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060308b     Document Type: Article

References (30)

1. (a) Wenzel, T. J.; Wilcox, J. D. Chirality 2003, 15, 256-270.
2. (b) Kasai, Y.; Taji, H.; Fujita, T.; Yamamoto, Y.; Akagi, M.; Sugio, A.; Kuwahara, S.; Watanabe, M.; Harada, N.; Ichikawa, A.; Schurig, V. Chirality 2004, 16, 569-585.
3. (c) Kusumi, T.; Yabuuchi, T.; Takahashi, H.; Ooi, T. J. Synth. Org. Chem. Jpn. 2005, 63, 1102-1114.
4. For reviews, see: (a) Topics in Current Chemistry, Schulz, S., Ed.; Springer: Berlin, 2004; Vol. 239.
5. (b) Topics in Current Chemistry; Schulz, S., Ed.; Springer: Berlin, 2005; Vol. 240.
6. Jacques, J.; Fouquey, C. Organic Syntheses: Wiley & Sons: New York, 1989; Vol. 67, pp 1-12.
7. 3, and secondary alcohols: (a) Kato, N. J. Am. Chem. Soc. 1990, 112, 254-257.
8. (b) Kato, N.; Iguchi, M.; Kato, Y. Tetrahedron: Asymmetry 1991, 2, 763-766.
9. Naidu, M. S. R.; Bull, E. O. J.; Nagaraju, C. Indian J. Chem. 1990, 29B, 691-693.
10. For descriptions of the use of phosphorus-containing CDAs for the evaluation of chiral alcohols, see: (a) Alexakis, A.; Mutti, S.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 437-440.
11. (b) Hulst, R.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 699-708.
12. (c) Bredikhin, A. A.; Bredikhina, Z. A.; Nigmatzyanov, F. F. Russ. Chem. Bull. 1998, 47, 411-416.
13. (d) Bredikhin, A. A.; Bredikhina, Z. A.; Gaisina, E. M.; Strunskaya, E. I.; Azancheev, N. M. Russ. Chem. Bull. 2000, 49, 310-313.
14. (e) Alexakis, A.; Chauvin, A.-S. Tetrahedron: Asymmetry 2000, 11, 4245-4248.
15. (f) Reymond, S.; Brunel, J. M.; Buono, G. Tetrahedron: Asymmetry 2000, 11, 1273-1278.
16. (g) Weix, D. J.; Dreher, S. D.; Katz, T. J. J. Am. Chem. Soc. 2000, 122, 10027-10032.
17. (h) Li, K. Y.; Zhou, Z. H.; Chan, A. S. C.; Tang, C. C. Heteroat. Chem. 2002, 13, 93-95.
18. (i) Wang, D. Z.; Katz, T. J. J. Org. Chem. 2005, 70, 8497-8502.
19. For a description of CDAs bearing P=Se bond for the evaluation of chiral alcohols, see: House, K. E.; O'Connor, M. J.; Silks, E. A.; Dunlap, R. B.; Odom, J. D. Chirality 1994, 6, 196-201.
20. For descriptions of the use of selenium-containing CDAs for the evaluation of chiral alcohols, see: (a) Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron: Asymmetry 1995, 6, 833-834.
21. (b) Silks, E. A.; Wu, R.; Dunlap, R. B.; Odom, J. D. Phosphorus, Sulfur Silicon Relat. Elem. 1998, 136-138, 209-214.
22. See Supporting Information for details of the separation of esters 3a, 3c, 3d, and 3g.
23. The esters 3d with high diastereomeric excess were obtained by HPLC purification of the esters obtained in Scheme 1.
24. Since optically active 3-octanol is a known pheromone, its synthesis and isolation in enantiomerically pure form are important: (a) Cho, B. T.; Kim, D. J. Tetrahedron 2003, 59, 2457-2462.
25. (b) Ichikawa, A.; Ono, H. Tetrahedron: Asymmetry 2005, 16, 2559-2568.
26. 11b
27. 31P NMR spectra of esters 3d, formed by reactions of alcohols (S)-and (R)-2d with 1, each contain only a single signal.
28. Enantiomeric excess of amine 4 is determined by HPEC (chiralcel AD-H).
29. The absolute configurations of the amines 4 and 5 are assigned by comparison of their specific rotations with those reported, (a) For 4: Cannata, V.; Samori, B.; Tramontini, M. Tetrahedron 1971, 27, 5247-5254.
30. (b) For 5: Pyne, S. G.; Griffith, R.; Edwards. M. Tetrahedron Lett. 1988, 29, 2089-2092.