Efficient synthesis of a key intermediate of neurokinin receptor antagonists using a bifunctional asymmetric catalyst

Synlett

Volumn , Issue 3, 2003, Pages 353-356

  Takamura, Makoto ^a   Yabu, Kazuo ^a   Nishi, Takahide ^a   Yanagisawa, Hiroaki ^a   Kanai, Motomu ^b   Shibasaki, Masakatsu ^b  

^a DAIICHI SANKYO CO   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric; Catalysis; Ketones; Ligands; Titanium

Indexed keywords

2 (ARYLMORPHOLIN 2 YL)ETHANOL; KETONE; TACHYKININ RECEPTOR ANTAGONIST; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SILYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037289174     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37123     Document Type: Article

References (12)

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3. Nishi, T.; Ishibashi, K.; Nakajima, K.; Iio, Y.; Fukazawa, T. Tetrahedron: Asymmetry 1998, 9, 3251.
4. A synthetic method using iodoetherification and optical resolution was already reported: Takemoto, T.; Yukiko Iio, Y.; Nishi, T. Tetrahedron Lett. 2000, 41, 1785.
5. Hamashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412.
6. Clay, R. J.; Collom, T. A.; Karrick, G. L.; Wemple, J. Synthesis 1993, 290.
7. 3, δ in ppm): 0.02 (6 H, s), 0.16 (9 H, s), 0.84 (9 H, s), 2.08-2.15 (1 H, m), 2.20-2.28 (1 H, m), 3.60-3.66 (1 H, m), 3.73-3.79 (1 H, m), 7.35 (1 H, dd, J = 2.0 Hz, 8.5 Hz), 7.46 (1 H, d, J = 8.5 Hz), 7.60 (1 H, d, J = 2.0 Hz).
8. 2Si 364.1266).
9. Hamashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691.
10. Masumoto, S.; Yabu, K.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 2919.
11. Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908.
12. 3SiCN (60 μL, 1.5 equiv) was added at -40 °C. After stirring for 15 min, the reaction was started by adding a solution of ketone 3 (0.30 mmol) in EtCN (0.1 mL).