Catalytic Asymmetric Induction. Highly Enantioselective Addition of Dialkylzincs to Aldehydes Using Chiral Pyrrolidinylmethanols and Their Metal Salts

Journal of the American Chemical Society

Volumn 109, Issue 23, 1987, Pages 7111-7115

  Soai, Kenso ^a   Ookawa, Atsuhiro ^a   Kaba, Tatsuya ^a   Ogawa, Kazuo ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

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Indexed keywords

EID: 33845282537     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00257a034     Document Type: Article

References (9)

1. Mukaiyama, T.; Soai, K.; Kobayashi, S. Chem. Lett. 1978, 219. Soai, K.; Mukaiyama, T. J. Org. Chem. 1978, 491. Sato, T.; Soai, K.; Suzuki, K.; Mukaiyama, T. J. Org. Chem. 1978, 601. Mukaiyama, T.; Soai, K.; Suzuki, K.; Sato, T. J. Org. Chem. 1979, 447. Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979,101, 1455. Soai, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1979, 52, 3371. (b) Mazaleyrat, J. P.; Cram, D. J. J. Am. Chem. Soc. 1981,103, 4585. (c) Weidman, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 31. (d) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25. 5187. (e) Tomioka. K.: Nakaiima. M.;Koea. K. Chem. Lett. 1987. 65.
2. For reviews, see: Ojima, I.; Hirai, K. Asymmetric Synthesis; morrison, J. D., Ed.; Academic: Orlando, FL, 1985; Vol. 5, Chapter 4. Hayashi, T.; Kumada, M. Chem. Lett., Chapter 5. Bosnich, B. Asymmetric Catalysts; Martinus Niihoff Publishers: Dordrecht. 1986: Chanter 3.
3. Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823. (b) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (c) Smaardiik. Ab. A.: Wynberg. H. J. Ore. Chem. 1987. 52. 135.
4. Soai, K.; Ookawa, A. J. Chem. Soc., Chem. Commun. 1986, 412. Ookawa, A.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1987, 1465.
5. Soai, K.; Ookawa, A.; Ogawa, K.; Kaba T. J. Chem. Soc., Chem. Commun. 1987, 467.
6. Diethylzinc is known to react rapidly with primary, secondary, and tertiary alcohols to afford monoalkoxide. Further reaction of monoalkoxide with secondary and tertiary alcohols is slow. See: Ishimori, M.; Tsuruta, T. Makromol. Chem. 1963, 64, 190.
7. Pine, S. H.; Hendrickson, J. B.; Cram, D. J.; Hammond, G. S. Organic Chemistry. 4th ed.: McGraw-Hill: New York. 1980: Chanter 6.
8. Ho, T. L. Hard and Soft Acids and Bases Principle in Organic Chemistry; Academic: New York 1977; Chapter 2.
9. Ono, N.; Yamada, T.; Saito, T.; Tanaka, K.; Kaji, A. Bull. Chem. Soc. Jpn. 1978, 51 2401.