Enantioresolution and absolute stereochemistry of 3,3′-diacetyl-4,4′,6,6′-tetramethoxy-2,2′-biphenyldiol

Enantiomer

Volumn 2, Issue 5, 1997, Pages 353-358

  Harada, Nobuyuki ^a   Li, Hong Yu ^a   Nehira, Tatsuo ^a   Hagiwara, Mami ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

( ) Camphanic acid; 3,3 Diacetyl 4,4 ,6,6 tetramethoxy 2,2 biphenyldiol; Absolute stereochemistry; Chiral 2,2 biphenyldiol; Enantioresolution; HPLC separation; X ray crystallographic analysis

Indexed keywords

EID: 6744227323     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. N. Harada, H. Ono, H. Uda, M. Parveen, N.U.-D. Khan, B. Achari and P.K. Dutta, J. Am. Chem. Soc., 1992, 114, 7687-7692.
2. Recently, Chinese chemists claimed that the X-ray crystallographic analysis led to the absolute configuration opposite to that obtained by theoretical calculation of CD spectra reported in ref. [1]: F.-J. Zhang, G.-Q. Lin and Q.-C. Huang, J. Org. Chem., 1995, 60, 6427-6430.
3. However, the claim was later retracted: Additions and Corrections in J. Org. Chem., 1996, 61, 5700.
4. N. Harada, H.-Y. Li and T. Nehira, J. Org. Chem. 1997, 62, in press.
5. N. Harada, T. Soutome, T. Nehira, H. Uda, S. Oi, A. Okamura and S. Miyano, J. Am. Chem. Soc., 1993, 115, 7547-7548.
6. N. Harada, T. Nehira, T. Soutome, N. Hiyoshi and F. Kido, Enantiomer, 1996, 1, 35-39.
7. See also: S. Toyota, A. Yasutomi and M. Oki, Tetrahedron Lett., 1995, 36, 6297-6300.
8. N. Harada, N. Koumura and M. Robillard, Enantiomer, 1997, 2, 303-309
9. N. Harada, N. Hiyoshi, V.P. Vassilev and T. Hayashi, Chirality, 1997, in press.
10. N. Harada, V.P. Vassilev and N. Hiyoshi, Enantiomer, 1997, 2, 123-126
11. H. Nemoto, J. Miyata, K. Fukumoto, H. Ehara, N. Harada, H. Uekusa and Y. Ohashi, Enantiomer, 1997, 2, 127-131.
12. 3).
13. W.L. Meyer, A.P. Lobo and R.N. McCarty, J. Org. Chem., 1967, 32, 1754-1762.
14. 14 750.28870, found 750.28845.
15. 14 750.28870, found 750.28910.
16. 0), 4308. The absolute configuration of 4b was determined by the internal reference method using the absolute configuration of the camphanate ester moiety.
17. 0), 3552.
18. 8 390.13144, found 390.13128.
19. 3 (0.4 mL) exhibited two peaks of acetyl group: δ 2.716 ppm for (aS)-2; δ 2.747 ppm for (aR)-2.