2-Anthrylmethoxyacetic acid, a new chiral anisotropic reagent for elucidating the absolute configuration of acyclic alcohols

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4541-4544

  Kouda, Kyoji ^a   Kusumi, Takenori ^a   Ping, Xu ^b   Kan, Yukiko ^c   Hashimoto, Toshihiro ^c   Asakawa, Yoshinori ^c  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^c TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE;

ANISOTROPY; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ESTERIFICATION;

EID: 0030600175     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00898-2     Document Type: Article

References (9)

1. 1. (a) Kusumi, T.; Takahashi, H.; Ping, X.; Fukushima, T.; Asakawa, Y.; Hashimoto, T.; Kan, Y. Tetrahedron Lett., 1994, 35, No. 25, 4397-4400.
2. (b) Kusumi, T.; Takahashi, H.; Hashimoto, T.; Kan, Y.; Asakawa, Y. Chemistry Lett., 1994, 1093-1094.
3. 2. Latypov, Sh. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Org. Chem., 1995, 60, 504-515.
4. 3. 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, 51, 2370-2374.
5. 4. Arjunan, P.; Berlin, K. D.; Shymasundar, N.; Najjar, D.; Rockley, M. G. J. Org. Chem., 1981, 46, 626-629.
6. 5. Compere, Jr., E.L.; Shockravi, A.; J. Org. Chem., 1978, 43, 2702-2703.
7. 6. (S)-2ATMA: CD (MeOH) λext 254.8 nm (Δε +13.2). (R)-2ATMA: CD (MeOH) λext 253.8 nm (Δε -11.5).
8. 7. Watanabe, H. Yakugakuzassi, 1953, 73, 176-179.
9. 8. Spectrum (a) of (S)-2ATMA ester of ginnol also exhibits two methyl signals at δ 0.869 and 0.881. We at first thought that the anisotropic effect of 2ATMA reached 29-Me. However, the distance from the 2ATMA moiety, 19-bonds apart, is so long that we now believe that the difference in chemical shift of the two methyl groups is due to the small upfield shift of 1-Me, intrinsically caused by the 2ATMA group, even though the anthryl moiety is directed toward the opposite side.