A Facile Synthesis of (R)-4-Amino-3-hydroxybutanoic Acid (GABOB) from 3-Hydroxypyridine

Synlett

Volumn 1997, Issue 2, 1997, Pages 221-222

  Sakagami, Hideki ^a   Kamikubo, Takashi ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001566510     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-744     Document Type: Article

References (12)

1. Sakagami, H.; Kamikubo, T.; Ogasawara, K. Chem. Commun. 1996, 1433.
2. a) Fowler, F. W. J. Org. Chem. 1972, 37, 1321.
3. b) Sundberg, R. J.; Hamilton, G.; Trindle, C. J. Org. Chem. 1986, 51, 3672.
4. A pertinent monograph, see: Wong, C. -H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
5. Ushikoba, K. Nippon Seirigaku Zasshi 1959, 21, 616.
6. The previous synthesis of (R)-4-amino-3-hydroxybutanoic acid (GABOB) by the author's group, see: Takano, S.; Yanase, M.; Sekiguchi, Y.; Ogasawara, K. Tetrahedron Lett. 1987, 28, 1783.
7. The most recent synthesis of (R)-4-amino-3-hydroxybutanoic acid (GABOB), see: Lohray, B. B.; Reddy, A. S.; Bhushan, V. Tetrahedron: Asymmetry 1996, 7, 2411.
8. 3) (>99% ee) as a colorless oil.
9. (a) Mitsunobu, O. Synthesis 1981, 1.
10. (b) Hughes, D. L. Org. Reactions 1992, 42, 335.
11. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
12. Braun, M.; Waldmüller, D. Synthesis 1989, 856.