A novel synthesis of chiral 1-allyl-1,2,3,4-tetrahydro-β-carboline employing allyltributyltin and chiral acyl chlorides

Synlett

Volumn , Issue 11, 1999, Pages 1799-1801

  Itoh, Takashi ^a   Matsuya, Yûji ^a   Enomoto, Yasuko ^a   Nagata, Kazuhiro ^a   Miyazaki, Michiko ^a   Ohsawa, Akio ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

2,2,2 trichloroethyl chloroformate; Allyltributyltin; Asymmetric addition; Chiral acyl chloride; carboline

Indexed keywords

BETA CARBOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032756361     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2952     Document Type: Article

References (22)

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2. a) Itoh, T.; Hasegawa, H.; Nagata, K.; Ohsawa, A. J. Org. Chem., 1994, 59, 1319.
3. b) Itoh, T.; Matsuya, Y.; Hasegawa, H.; Nagata, K.; Okada, M.; Ohsawa, A. J. Chem. Soc., Perkin Trans. 1, 1996, 2511.
4. Itoh, T.; Miyazaki, M.; Nagata, K.; Hasegawa, H.; Ohsawa, A.; Nakamura, K. T. Heterocycles, 1998, 47, 125.
5. The Chemistry of Heterocyclic Compounds, Saxton, J. E. Ed.; John Wiley & Sons: Chichester, 1994, Part 4, suppl. of Vol. 25.
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7. a) Martin, S. F.; Benage, B.; Hunter, J. E. J. Am. Chem. Soc., 1988, 110, 5925.
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9. a) Yamaguchi, R.; Otsuji, A.; Utimoto, K.; Kozima, S. Bull. Chem. Soc. Jpn., 1992, 65, 298.
10. b) Yamaguchi, R.; Hamasaki, T.; Sasaki, T.; Ohta, T.; Utimoto, K.; Kozima, S.; Takaya, H. J. Org. Chem., 1993, 58, 1136.
11. For the recent applications for the achiral 1,2-additions, see, a) Birman, V. B.; Rawal, V. H. Tetrahedron Lett., 1998, 39, 7219.
12. b) Birman, V. B.; Rawal, V. H. J. Org. Chem., 1998, 63, 9146.
13. Yamaguchi et al. reported in a review that benzyl 3,4-dihydro-β-carboline-3-(S)-carboxylate underwent the addition reaction with acryloyl chloride and tributyl(2,4-pentadienyl)tin to give yohimban derivatives in 83% yield (86% de). Yamaguchi, R. Yuki Gosei Kagaku Kyokaishi, 1991, 49, 128.
14. a) Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc., 1988, 110, 4778.
15. b) Meyers, A. I.; Highsmith, T. K.; Buonora, P. T. J. Org. Chem., 1991, 56, 2960, and references cited therein.
16. Itoh, T.; Nagata, K.; Miyazaki, M.; Ohsawa, A. Synlett, 1999, 1154.
17. Compound 1 could not be acylated at N-9 under usual conditions, thus the experiment parallel to 3 → 4 could not be carried out.
18. Other amino acids such as alanine, phenylalanine, valine, etc., were used for the reaction, but the de at step B was lower than that of proline derivatives.
19. Step A of Scheme 2 proceeded by the use of one eq. of acyl chloride and two eq. of triethylamine in THF at room temperature for 2-4 h. All the isolated yields were above 80%, and the details will be reported in a near future.
20. The other solvents such as 1,2-dichloroethane, acetonitrile, toluene, and DMF were used for the reaction, and dichloromethane was found to afford the best results.
21. The ee was monitored on a chiral HPLC, and it was found that no racemization occurred in the transformation of 8 to 10.
22. 2 to give 1-allyl-1,2,3,4-tetrahydro-2-(trans-2,4-pentadienoyl)-β-carboline in 75% yield. The compound was allowed to react with methoxymethyl chloride in the presence of potassium hydride to give the product without racemization.