Catalytic Asymmetric Aldol Reaction via Chiral Pd(II) Enolate in Wet DMF

Journal of Organic Chemistry

Volumn 60, Issue 9, 1995, Pages 2648-2649

  Sodeoka, Mikiko ^a   Ohrai, Kazuhiko ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000263137     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00114a002     Document Type: Article

References (16)

1. Rh catalysts: Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517.
2. Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938.
3. Soga, T.; Takenoshita, H.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1990, 63, 3122.
4. Pd catalysts: Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 4126.
5. Ru catalysts: Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S. J. Am. Chem. Soc. 1989, 111, 5954 and references cited therein.
6. Au(I) and Ag(I) complexes have been reported to catalyze the asymmetric aldol-type reaction of isonitriles with aldehydes. See: Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
7. Recently, the Pd(II) complex-catalyzed reaction of isonitriles has also been reported (maximum 14% ee); see: Nesper, R.; Pregosin, P. S.; Ptintener, K.; Worle, M. Helo. Chim. Acta 1993, 76, 2239 and references cited therein.
8. Reetz, M. T.; Vougioukas, A. E. Tetrahedron Lett., 1987, 28, 793 (maximum ee, 12%).
9. Roos, G. H. P.; Haines, R. J.; Raab, C. E. Synth. Commun. 1993, 23, 1251 (maximum ee, 23%).
10. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188.
11. The ee of 4 was determined by HPLC analysis using Chiralcel OJ, hexane:‘ PrOH 9:1, after conversion to 5 (1 N HC1-THF, 1:2). The absolute stereochemistry was determined to be R by comparison of the optical rotation of 4 (+32.4° (c 0.74, MeOH) (70% ee)) with the reported value. See: Mashraqui, S. H.; Kellogg, R. M. J. Org. Chem. 1984, 49, 2513.
12. For transition metal hydroxo complex, see: Woerpel, K. A.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 7888 and references cited therein.
13. Burkhardt, E. R.; Doney, J. J. D.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 109, 2022.
14. Aldol reactions catalyzed by transition metal Lewis acids have been reported; see: Cozzi, P. G.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Synlett 1994, 857 and references cited therein.
15. Ito, Y.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
16. For a review of the Lewis acid-catalyzed asymmetric Mu kaiyama aldol reaction, see: Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417 and references cited therein.