Asymmetric alkylation reaction of α-fluorotetralone under phase-transfer catalyzed conditions

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6785-6789

  Arai, Shigeru ^a   Oku, Makoto ^a   Ishida, Toshimasa ^b   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

Alkylation; Asymmetric synthesis; Catalysts; Phase transfer

Indexed keywords

CINCHONINE; FLUORINE DERIVATIVE; KETONE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; DRUG SYNTHESIS; PHASE TRANSITION; REACTION ANALYSIS;

EID: 0033543524     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01282-4     Document Type: Article

References (13)

1. Recently, efficient enantioselective fluorination of carbanions was reported, see: (a) Differding, E.; Lang, R. W. Tetrahedron Lett. 1988, 29, 6087-6090.
2. (b) Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przeslawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org. Chem. 1998, 63, 2273-2280.
3. (c) Takeuchi, Y.; Satoh, A.; Suzuki, T.; Kameda, A.; Dohrin, M.; Satoh, T.; Koizumi, T.; Kirk, K. L. Chem. Pharm. Bull. 1997, 45, 1085-1088.
4. (a) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148.
5. (b) Arai, S.; Shirai, Y.; Ishida, T.; Shioiri, T. Chem. Commun. 1999, 49-50.
6. (a) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563-7566.
7. (b) Arai, S.; Oku, M.; Miura, M.; Shioiri, T. Synlett 1998, 1201-1202.
8. Recently, successful results of asymmetric alkylation under PTC conditions were reported, see: (a) Manabe, K. Tetrahedron Lett. 1998, 39, 5807-5810.
9. (b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415, and references cited therein.
10. Substrate 1 was easily prepared according to the following procedure, see: Umemoto, T.; Nagayoshi, M.; Adachi, K.; Tomizawa, G. J. Org. Chem. 1998, 63, 3379-3385.
11. Cf. Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745-4752.
12. Cortese, N. A.; Heck, R. F. J. Org. Chem. 1977, 42, 3491-3494.
13. Modified procedure was reported, see: Nunez, M. T.; Martin, V. S. J. Org. Chem. 1990, 55, 1928-1932, and references cited therein.