New and improved ligands for highly enantioselective catalytic diphenylzinc additions to aryl aldehydes

Tetrahedron Letters

Volumn 41, Issue 2, 2000, Pages 145-149

  Huang, Wei Sheng ^a   Pu, Lin ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; REACTION ANALYSIS;

EID: 0034620204     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02041-9     Document Type: Article

References (28)

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7. For the enantioselective reaction of stoichiometric or excess chiral organometallic aryl compounds with aryl aldehydes, see: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597. (c) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (d) Kaino, M.; Ishihara, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 3736. (e) Wang, J.-T.; Fan, X.; Feng, X.; Qian, Y.-M. Synthesis 1989, 291. (f) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1991, 49, 9751. (g) An in situ generated phenylzinc reagent was added to aryl aldehydes in the presence of a stoichiometric amount of a chiral ligand: Soai, K.; Kawase, Y.; Oshio, A. J. Chem. Soc. Perkin Trans. 1 1991, 1613.
8. For the enantioselective reaction of stoichiometric or excess chiral organometallic aryl compounds with aryl aldehydes, see: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597. (c) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (d) Kaino, M.; Ishihara, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 3736. (e) Wang, J.-T.; Fan, X.; Feng, X.; Qian, Y.-M. Synthesis 1989, 291. (f) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1991, 49, 9751. (g) An in situ generated phenylzinc reagent was added to aryl aldehydes in the presence of a stoichiometric amount of a chiral ligand: Soai, K.; Kawase, Y.; Oshio, A. J. Chem. Soc. Perkin Trans. 1 1991, 1613.
9. For the enantioselective reaction of stoichiometric or excess chiral organometallic aryl compounds with aryl aldehydes, see: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597. (c) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (d) Kaino, M.; Ishihara, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 3736. (e) Wang, J.-T.; Fan, X.; Feng, X.; Qian, Y.-M. Synthesis 1989, 291. (f) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1991, 49, 9751. (g) An in situ generated phenylzinc reagent was added to aryl aldehydes in the presence of a stoichiometric amount of a chiral ligand: Soai, K.; Kawase, Y.; Oshio, A. J. Chem. Soc. Perkin Trans. 1 1991, 1613.
10. For the enantioselective reaction of stoichiometric or excess chiral organometallic aryl compounds with aryl aldehydes, see: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597. (c) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (d) Kaino, M.; Ishihara, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 3736. (e) Wang, J.-T.; Fan, X.; Feng, X.; Qian, Y.-M. Synthesis 1989, 291. (f) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1991, 49, 9751. (g) An in situ generated phenylzinc reagent was added to aryl aldehydes in the presence of a stoichiometric amount of a chiral ligand: Soai, K.; Kawase, Y.; Oshio, A. J. Chem. Soc. Perkin Trans. 1 1991, 1613.
11. For the enantioselective reaction of stoichiometric or excess chiral organometallic aryl compounds with aryl aldehydes, see: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597. (c) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (d) Kaino, M.; Ishihara, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 3736. (e) Wang, J.-T.; Fan, X.; Feng, X.; Qian, Y.-M. Synthesis 1989, 291. (f) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1991, 49, 9751. (g) An in situ generated phenylzinc reagent was added to aryl aldehydes in the presence of a stoichiometric amount of a chiral ligand: Soai, K.; Kawase, Y.; Oshio, A. J. Chem. Soc. Perkin Trans. 1 1991, 1613.
12. For the enantioselective reaction of stoichiometric or excess chiral organometallic aryl compounds with aryl aldehydes, see: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597. (c) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (d) Kaino, M.; Ishihara, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 3736. (e) Wang, J.-T.; Fan, X.; Feng, X.; Qian, Y.-M. Synthesis 1989, 291. (f) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1991, 49, 9751. (g) An in situ generated phenylzinc reagent was added to aryl aldehydes in the presence of a stoichiometric amount of a chiral ligand: Soai, K.; Kawase, Y.; Oshio, A. J. Chem. Soc. Perkin Trans. 1 1991, 1613.
13. For the enantioselective reaction of stoichiometric or excess chiral organometallic aryl compounds with aryl aldehydes, see: (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597. (c) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65. (d) Kaino, M.; Ishihara, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 3736. (e) Wang, J.-T.; Fan, X.; Feng, X.; Qian, Y.-M. Synthesis 1989, 291. (f) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1991, 49, 9751. (g) An in situ generated phenylzinc reagent was added to aryl aldehydes in the presence of a stoichiometric amount of a chiral ligand: Soai, K.; Kawase, Y.; Oshio, A. J. Chem. Soc. Perkin Trans. 1 1991, 1613.
14. Weber, B.; Seebach, D. Tetrahedron 1994, 50,7473.
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17. (a) Huang, W.-S.; Pu, L. J. Org. Chem. 1999, 64, 4222.
18. (b) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1999, 64, 7940.
19. Bolm, C.; Muniz, K. Chem. Commun. 1999, 1295.
20. Selected references on the Suzuki coupling: (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Comm. 1981, 11, 513. (b) Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411. (c) Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
21. Selected references on the Suzuki coupling: (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Comm. 1981, 11, 513. (b) Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411. (c) Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
22. Selected references on the Suzuki coupling: (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Comm. 1981, 11, 513. (b) Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411. (c) Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
23. Compound (S)-3 was synthesized by treatment of (S)-2,2′-dimethoxymethoxy-1,1′-binaphthyl with n-butyllithium in diethyl ether at room temperature followed by addition of 2-isopropoxy-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane. Hu, Q.-S.; Pu, L. unpublished results.
24. Similar transition states have been proposed previously for amino alcohol-catalyzed diethylzinc additions to aldehydes: Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
25. Lutz, C.; Graf, C.-D.; Knochel, P. Tetrahedron 1998, 54, 10317.
26. Wu, B.; Mosher, H. S. J. Org. Chem. 1986, 51, 1904.
27. Brown, E.; Leze, A.; Touet, J. Tetrahedron: Asymmetry 1992, 3, 841.
28. Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1998, 46, 577.