Asymmetric addition of dialkylzincs to benzaldehyde derivatives catalyzed by chiral β-amino alcohols. Evidence for the monomeric alkylzinc aminoalkoxide as catalyst

Tetrahedron

Volumn 55, Issue 12, 1999, Pages 3605-3614

  Kitamura, Masato ^a   Hiromasa, Oka ^a   Noyori, Ryoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINOALCOHOL; BENZALDEHYDE DERIVATIVE; ISOBORNEOL; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; ENANTIOMER; METHYLATION; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOSPECIFICITY; TURNOVER TIME;

EID: 0033583015     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01167-3     Document Type: Article

References (42)

1. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072. Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko. T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19-37. For the first report on the amino alcohol promoted asymmetric ethylation of benzaldehyde, see: Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823-2824.
2. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072. Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko. T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19-37. For the first report on the amino alcohol promoted asymmetric ethylation of benzaldehyde, see: Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823-2824.
3. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072. Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko. T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19-37. For the first report on the amino alcohol promoted asymmetric ethylation of benzaldehyde, see: Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823-2824.
4. Review: Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69.
5. Noyori, R.; Suga, S.; Kawai, K.; Okada. S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597-1606.
6. Oguni, N.: Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877-7878.
7. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191-1203.
8. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
9. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
10. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
11. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
12. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
13. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
14. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
15. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
16. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
17. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
18. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
19. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
20. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
21. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
22. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
23. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
24. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
25. Early reports on the nonlinear effect in asymmetric reactions. Sharpless epoxidation of geraniol and oxidation of sulfides: Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357. Hajos-Wiechert intramolecular aldol reaction: Agami, C.; Levisalles, J.; Puchot, C. J. Chem. Soc., Chem. Commun. 1985, 441-442. Agami, C. Bull. Soc: Chim. Fr. 1988, 499-507. Other asymmetric reactions showing nonlinear effect. Oxidation of sulfides: Komatsu, N.; Hashizume, M.; Sugita, T.: Uemura. S. J. Org. Chem. 1993, 58, 4529-4533. Meerwein-Ponndorf-Verley reduction: Evans, D. A.; Nelson, S. G.; Gagné, M. R.: Muci, A. R. J. Am. Chem. Soc.1993, 115, 9800-9801. Reduction of acetophenone by diisopinocamphenyl chloroborate: Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1997. 8, 3851-3854. Ene reaction: Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834. Diels-Alder reaction: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584. Mikami, K.; Moloyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328. Silylcyanation of benzaldehyde: Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365. Conjugate addition of organometallics to α,β-unsaturated carbonyl compounds: Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-137. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.: Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491. Nitro-aldol reaction: Sasai, H.; Suzuki. T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854. Allylation of aldehydes using organotin compounds: Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
26. 8
27. Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
28. Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832-4842.
29. Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R.; Zhai, Z.-X.; Suga, H. J. Phys. Chem. 1994, 98, 12776-12781.
30. Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327-6335.
31. Evans, D. A. Science 1988, 240, 420-426.
32. Corey, E. J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784-786.
33. For the structural origin of the differences of the homochiral and heterochiral dimers, see: Kitamura, M.; Yamakawa, M.; Oka, H.; Suga. S.; Noyori, R. Chem. Eur. J. 1996, 2, 1173-1181.
34. Guillaneux, D.; Zhao, S.-H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430-9439. In Kagan's reservoir effect, catalytic species are considered to be preserved as their associates. See also, Blackmond, D. G. J. Am. Chem. Soc. 1997, 119, 12934-12939.
35. Guillaneux, D.; Zhao, S.-H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430-9439. In Kagan's reservoir effect, catalytic species are considered to be preserved as their associates. See also, Blackmond, D. G. J. Am. Chem. Soc. 1997, 119, 12934-12939.
36. For the nonlinear effect based on catalyst activation, see: Matsukawa, S.; Mikami, K. Enantiomer 1996, 1, 69-73. Mikami, K.; Matsukawa, S. Nature 1997,385, 613-615. Ohkuma T.; Doucet, H.; Pham, T.; Mikami, K.; Korenaga, T.; Terada, M.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 1086-1087.
37. For the nonlinear effect based on catalyst activation, see: Matsukawa, S.; Mikami, K. Enantiomer 1996, 1, 69-73. Mikami, K.; Matsukawa, S. Nature 1997,385, 613-615. Ohkuma T.; Doucet, H.; Pham, T.; Mikami, K.; Korenaga, T.; Terada, M.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 1086-1087.
38. For the nonlinear effect based on catalyst activation, see: Matsukawa, S.; Mikami, K. Enantiomer 1996, 1, 69-73. Mikami, K.; Matsukawa, S. Nature 1997,385, 613-615. Ohkuma T.; Doucet, H.; Pham, T.; Mikami, K.; Korenaga, T.; Terada, M.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 1086-1087.
39. The dimer mechanism of Figure 2 should be seriously considered under some special conditions, e.g. at very high concentrations of the catalyst and reactants.
40. Noller, C. R. Org. Synth. Collective Vol. 1943, 2, 184-187.
41. Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Hoogsteen, K.; Carroll, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 2880-2888.
42. Brown, H. C.; Cho, B. T.; Park, W. S. J. Org. Chem. 1988, 53, 1231-1238.