Asymmetric reduction of ketoxime ethers to optically O-substituted hydroxylamines with reagents prepared from borane and chiral amino alcohols

Tetrahedron Asymmetry

Volumn 8, Issue 4, 1997, Pages 497-499

  Dougherty, John T ^a   Flisak, Joseph R ^a   Hayes, Jerome ^a   Lantos, Ivan ^a   Liu, Li ^a   Tucker, Lynn ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; HYDROXYLAMINE; NOREPHEDRINE; OXIME DERIVATIVE; REAGENT;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REDUCTION;

EID: 0031579451     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00007-4     Document Type: Article

References (12)

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2. b) Itsuno, S.; Sakurai, Y.; Shimizu, K.; Ito, K. J. Chem. Soc. Perkin Trans. 1 1989, 1548-1549.
3. c) Itsuno, S.; Sakurai, Y.; Shimizu, K.; Ito, K. J. Chem. Soc. Perkin Trans. 1 1990, 1859-1863.
4. d) Itsuno, S.; Nakano, M.; Ito, K. J. Chem. Soc. Perkin Trans. 1 1985, 2615-2619.
5. e) Itsuno, S.; Tanaka, K.; Ito, K. Chem. Lett. 1986, 1133-1136.
6. f) Gibbs, D. E.; Barnes, D. Tetrahedron Lett. 1990, 31, 5555-5558.
7. g) Tillyer, R. D.; Boudreau, C.; Tschaen, D.; Dolling, U.-H.; Reider, P. J. Tetrahedron Lett. 1995, 36, 4337-4340.
8. h) Cho, B. T.; Ryu, M. H. Bull. Korean Chem. Soc. 1994, 15(3), 191-192.
9. 2. In their description of the asymmetric reduction of oxime ethers to amines, Suzukamo et al. allude to the possibility of obtaining methyl ethers of hydroxylamines, which were not characterized (Table 1 notes); Sakito, Y.; Yoneyoshi, Y.; Suzukamo, G. Tetrahedron Letters 1988, 223-224.
10. 3. a) Corey, E. J.; Bakshi, R. K.; Shibita, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
11. b) Corey, E. J.; Bakshi, R. K.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926.
12. 4. The absolute configuration of 4c was determined as (3S) in contrast to the same compound prepared from (S)-N-(6-benzyloxy-2,3-dihydrobenzofuran-3-yl)-hydroxylamine which structure has been determined by X-ray.