Asymmetric catalytic alkylation of aldehydes with diethylzinc using a chiral binaphthol-titanium complex

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6233-6236

  Mori, Maki ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; TITANIUM DERIVATIVE; ZINC;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030752318     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01433-0     Document Type: Article

References (14)

1. Reviews: (a) Mikami, K. ; Terada, M. ; Narisawa, S. ; Nakai, T. Synlett 1992, 255-265. (b) Mikami, K. ; Terada, M. ; Narisawa, S. ; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press, Inc: London, 1995; 1, p 123-149.
2. Reviews: (a) Mikami, K. ; Terada, M. ; Narisawa, S. ; Nakai, T. Synlett 1992, 255-265. (b) Mikami, K. ; Terada, M. ; Narisawa, S. ; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press, Inc: London, 1995; 1, p 123-149.
3. Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861-1864.
4. Imma, H.; Mori, M.; Nakai, T. Synlett 1996, 12, 1229-1230.
5. Mori, M.; Imma, H.; Nakai, T., the preceding paper.
6. For the asymmetric catalytic alkylations of aldehydes with organozinc reagents using chiral titanium catalysts in particular, see:(a) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363-4384. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691-5700. (c) Soai, K.; Niwa, S. Chem. Rev. 1992, 92. 833-856. (d) Soai, K.; Hayase, T. J. Synth. Org. Chem., Jpn. 1995, 53, 138-150.
7. For the asymmetric catalytic alkylations of aldehydes with organozinc reagents using chiral titanium catalysts in particular, see:(a) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363-4384. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691-5700. (c) Soai, K.; Niwa, S. Chem. Rev. 1992, 92. 833-856. (d) Soai, K.; Hayase, T. J. Synth. Org. Chem., Jpn. 1995, 53, 138-150.
8. For the asymmetric catalytic alkylations of aldehydes with organozinc reagents using chiral titanium catalysts in particular, see:(a) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363-4384. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691-5700. (c) Soai, K.; Niwa, S. Chem. Rev. 1992, 92. 833-856. (d) Soai, K.; Hayase, T. J. Synth. Org. Chem., Jpn. 1995, 53, 138-150.
9. For the asymmetric catalytic alkylations of aldehydes with organozinc reagents using chiral titanium catalysts in particular, see:(a) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363-4384. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691-5700. (c) Soai, K.; Niwa, S. Chem. Rev. 1992, 92. 833-856. (d) Soai, K.; Hayase, T. J. Synth. Org. Chem., Jpn. 1995, 53, 138-150.
10. After this work was presented at the 70th Annual Meeting of the Chemical Society of Japan, March, 1996, Tokyo, Abstract 1J305, Chan and his co-workers have recently reported the addition reaction of diethylzinc to aromatic aldehydes catalyzed by essentially the same BINOL-Ti complex as reported herein: Zhang, F.-Y.; Yip, C-W.; Cao, R.; Chan, A. S. C. Tetrahedron:Asymm. 1997, 8, 585-589. This publication prompted us to disclose our own results which include the reactions with aliphatic aldehydes and more detailed mechanistic aspects of this reaction.
11. 4Cl soln., the mixture was allowed to slowly warm up to room temperature and was then filtered through Celite to remove the solid formed. Usual workup followed by silica gel column chromatography afforded the corresponding alcohol. The enantiomeric purity was determined by GC on chiral column.
12. A dimeric structure has been reported for the crystal structure of complex A: Martin, C. A. Ph. D. Thesis, MIT, 1988. Cf. Imma, H. Master Thesis, Tokyo Institute of Technology, 1995.
13. A dimeric structure has been reported for the crystal structure of complex A: Martin, C. A. Ph. D. Thesis, MIT, 1988. Cf. Imma, H. Master Thesis, Tokyo Institute of Technology, 1995.
14. The dichiral complex E, if it acts as a precatalyst, should provide a different %ee from that of the monochiral complex F, thus the overall %ee depending, more or less, on %conversion.