Lipase-Catalyzed Kinetic Resolution of 4-(N-Boc-amino)-1-alken-3-ols

Synlett

Volumn , Issue 15, 2003, Pages 2374-2376

  Oshitari, Tetsuta ^a   Mandai, Tadakatsu ^a  

^a KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

4 (N Boc amino) 1 alken 3 ols; Kinetic resolution; Lipase; The taxol side chain

Indexed keywords

ALKENE DERIVATIVE; AMINOALCOHOL; NATURAL PRODUCT; PACLITAXEL DERIVATIVE; TOLUENE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; TEMPERATURE;

EID: 0346749661     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42115     Document Type: Article

References (27)

1. Gargano, J. M.; Lees, W. J. Tetrahedron Lett. 2001, 42, 5845; and references therein.
2. (a) Umezawa, H.; Aoyagi, T.; Morishima, H.; Matsuzaki, M.; Hamada, M.; Takeuchi, T. J. Antibiot. 1970, 23, 259.
3. (b) Yoo, D.; Oh, J. S.; Kim, Y. G. Org. Lett. 2002, 4, 1213; and references therein.
4. Jost, S.; Gimbert, Y.; Green, A. E.; Fotiadu, F. J. Org. Chem. 1997, 62, 6672; and references therein.
5. (a) Sobin, B. A.; Tanner, F. W. Jr. J. Am. Chem. Soc. 1954, 76, 4053.
6. (b) Hulme, A. N.; Rosser, E. M. Org. Lett. 2002, 4, 265; and references therein.
7. (a) Kulanthaivel, P.; Hallock, Y. F.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. M.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 6452.
8. (b) Fürstner, A.; Thiel, O. R. J. Org. Chem. 2000, 65, 1738; and references therein.
9. (a) Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175.
10. (b) Kikuchi, H.; Tasaka, H.; Hirai, S.; Takaya, Y.; Iwabuchi, Y.; Ooi, H.; Hatakeyama, S.; Kim, H.-S.; Wataya, Y.; Oshima, Y. J. Med. Chem. 2002, 45, 2563; and references therein.
11. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
12. (a) Review: Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 103.
13. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
14. (c) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483.
15. Mandai, T.; Oshitari, T.; Susowake, M. Synlett 2002, 1665.
16. Prepared as shown below (Scheme 4).
17. The enantiomeric purities of (3R,4R)-1-OAc, (35,45)-1, (3R,4S)-2-OAc, and (3S,4R)-2 were analyzed by HPLC (Chiralcel OD-H or Chiralcel OJ-H, hexane-2-propanol) after being converted to suitably protected compounds as described below (Figure 1). (Equation Presented) Figure 1 1a: R′ = CONHPh, OD-H, 50:1, 230 nm; 1b: R′ = CON-HPh, OD-H, 30:1, 230 nm; 1c: R′ = CONHPh, OD-H, 20:1, 254 nm; 1d: R′ = Bz, OD-H, 50:1, 254 nm; 1e: R′ = H, OJ-H, 50:1, 230 nm; 2a: R′ = Bz, OD-H, 50:1, 254 nm; 2b: R′ = Bz, OD-H, 50:1, 254 nm; 2c: R′ = H, OD-H, 20:1, 230 nm; 2d: R′ = H, OD-H, 20:1, 230 nm; 2e: R′ = Bz, OD-H, 30:1, 254 nm.
18. 2) afforded (3R,4S)-2d-OAc (5.58 mmol, 49%) and (35,4R)-2d (5.59 mmol, 49%).
19. (a) Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
20. (b) Chen, C.-S.; Wu, S.-H.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1987, 109, 2812.
21. 3/MeOH, r.t., 40 min) to the corresponding alcohol (3R, 4R)-3, which was analyzed by HPLC (Chiralcel OD-H, hexane-2-propanol = 4:1, 254 nm). (3R,4S)-4-OAc and (3S,4R)-4 were converted to the corresponding phenyl carbamates (PhNCO/Py, r.t., 6 h), which were analyzed by HPLC (Chiralcel OD-H, hexane-2-propanol = 5:1, 254 nm). Ohno reported that the modification of a protecting group at amino moiety changes the enantioselectivity of esterase-catalyzed hydrolysis of esters: Ohno, M.; Kobayashi, S.; Iimori, T.; Wang, Y.-F.; Izawa, T. J. Am. Chem. Soc. 1981, 103, 2405.
22. (b) In our case, the reverse of the enantioselectivity was not observed.
23. 15b was subjected to Curtius reaction to give a trans cyclic carbamate as the sole product.
24. (b) Mulzer, J.; Segner, J.; Brüntrup, G. Tetrahedron Lett. 1977, 4651.
25. 3-MeOH, r.t., 12 h, 75%.
26. 3-MeOH, r.t., 40 min) provided the corresponding alcohol, which was analyzed by HPLC (Chiralcel OD-H, hexane-2-propanol = 20:1, 230 nm).
27. Wang, Z.-M.; Kolb, H. C.; Sharpless, K. B. J. Org. Chem. 1994, 59, 5104.