An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4447-4450

  Kitagawa, Osamu ^a   Izawa, Hirotaka ^a   Taguchi, Takeo ^a   Shiro, Motoo ^b  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BETULACEAE;

EID: 0030950922     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00928-3     Document Type: Article

References (10)

1. (a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132.
2. (b) Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610.
3. Atropselective reactions of axially twisted N-(o-t-butylphenyl)maleimides (σ-symmetric compounds) have been also reported. Ref. 1a and Kishikawa, K.; Tsuru, I.; Kohmoto, S.; Yamamoto, M. Yamada, K. Chem. Lett. 1994, 1605-1606.
4. (S)-O-Acetyl lactic acid was purchased from Kanto Chemicals Co.
5. 13C NMR spectra of 2a and 2b, the minor signals which may be due to existence of the amide C-N rotamers were also observed in a ratio of 20:1 and 10:1, respectively.
6. The low reactivity of this aniline with O-acetyl lactic acid may be attributed to the bulkiness of the ortho-tert-butyl group. On the other hand, although anilides 2a and 2b were obtained in quantitative yield from N-allyl-o-tert-butyl aniline and (S)-acetoxypropionyl chrolide (commercially available), the preparation of 3 through this method gave 3 with lower optical purity (82 %ee).
7. 21NO: C, 78.97; H, 8.70; N, 5.76. Found; C, 79.06; H, 8.55; N, 5.61.
8. Kitagawa, O.; Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1995, 36, 593-596.
9. Janssen, A. J. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1991, 47, 5513-5538.
10. The stereochemistry and ee of the major adduct 6 were determined on the basis of X-ray crystallography and HPLC analysis using CHIRALPAK AS column (1 % i-PrOH in hexane), respectively.