Development of catalytic asymmetric reactions via chiral palladium enolates

Chemical Record

Volumn 4, Issue 4, 2004, Pages 231-242

  Hamashima, Yoshitaka ^a,b   Sodeoka, Mikiko ^a,c,d,e,f  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c CHIBA UNIVERSITY   (Japan)

^d SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^e HOKKAIDO UNIVERSITY   (Japan)

^f HARVARD UNIVERSITY   (United States)

Author keywords

Asymmetric reaction; Enolate; Hydroxo ligand; Nucleophilicity; Palladium

Indexed keywords

CARBONYL DERIVATIVE; ESTER DERIVATIVE; ION; KETONE DERIVATIVE; LIGAND; METAL; PALLADIUM COMPLEX; PROTON; SILANE DERIVATIVE; TETRAMETHYLUREA; WATER;

ACIDITY; ALDOL REACTION; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHEMICAL ENVIRONMENT; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMOBILIZATION; LIQUID; MANNICH REACTION; METALLATION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; REVIEW; SILYLATION;

ALDEHYDES; CATALYSIS; ESTERS; KETONES; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 7044249276     PISSN: 15278999     EISSN: None     Source Type: Journal    
DOI: 10.1002/tcr.20017     Document Type: Review

References (88)

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2. Albéniz, A. C.; Espinet, P. In Encyclopedia of Inorganic Chemistry. R. B. King, Ed. Wiley: Chichester, 1994; Vol. 6, p. 3010.
3. (a) Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century. Wiley: Chichester, 2004.
4. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
5. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
6. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
7. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
8. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
9. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
10. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
11. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
12. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
13. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
14. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
15. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
16. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
17. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
18. For other selected examples: β-hydride elimination: (b) Ito, Y.; Hirao, T.; Saegusa, T. J Org Chem 1978, 43, 1011; CO insertion reaction: (c) Stille, J. K.; Wong, P. K. J Org Chem 1975, 40, 532; insertion reaction: (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J Am Chem Soc 1979, 101, 494; (e) Mori, M.; Kubo Y.; Ban, Y. Tetrahedron 1988, 44, 4321; (f) Ogoshi, S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai, S. J Org Chem 1993, 58, 9; reductive coupling: (g) Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J Am Chem Soc, 1980, 102, 6384. (h) Tsuji, J.; Minami, I. Acc Chem Res 1987, 20, 140. (i) Kosugi, M.; Takano, I.; Sakurai, M.; Sano, H.; Migita, T. Chem Lett 1984, 1221; (j) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull Chem Soc Jpn 1984, 57, 242; (k) Kosugi, M.; Negishi, Y.; Kameyama, M.; Migita, T. Bull Chem Soc Jpn 1985, 58, 3383; (l) Carfagna, C.; Musco, A.; Sallese, G. J Org Chem 1991, 56, 261. (m) Palucki, M.; Buchwald, S. L. J Am Chem Soc 1997, 119, 11108; (n) Hamann, B. C.; Hartwig, J. F. J Am Chem Soc 1997, 119, 12382; (o) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem Int Ed 1997, 36, 1740; (p) Culkin, D. A.; Hartwig, J. F. Acc Chem Res 2003, 36, 234.
19. (a) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J Org Chem 1995, 60, 2648;
20. (b) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463;
21. (c) Sodeoka, M.; Shibasaki, M. Pure Appl Chem 1998, 70, 411.
22. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
23. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
24. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
25. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
26. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
27. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
28. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
29. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
30. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
31. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
32. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
33. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
34. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
35. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
36. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
37. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
38. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
39. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
40. Selected examples of the non-enantioselective reactions via a putative late transition metal enolate. For aldol and Michael reactions: Co: (a) Orsini, F.; Pelizzoni, F.; Pulici, M. J Org Chem 1994, 59, 1; Ni: (b) Rhee, I.; Ryu, I.; Omura, H.; Murai, S.; Sonoda, N. Chem Lett 1979, 1435; Ni, Pd: (c) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30; (d) Masuyama, Y.; Sakai, T.; Kato, T.; Kurusu, Y. Bull Chem Soc Jpn 1994, 67, 2265; Pd: (e) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J Am Chem Soc 1989, 111, 4127; (f) Nokami, J.; Watanabe, H.; Mandai, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett 30, 4829; (g) Nesper, R.; Pregosin, P.S.; Püntener, K.; Wörle M. Helv Chim Acta 1993, 76, 2239; Rh: (h) Sato, S.; Matsuda, I.; Izumi, Y. Chem Lett 1985, 1875; (i) Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett 1986, 27, 5517; (j) Aoyama, Y.; Tanaka, Y.; Yoshida, T.; Toi, H.; Ogoshi, H. J Organomet Chem 1987, 329, 251; (k) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J Am Chem Soc 1989, 111, 938; (l) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett 1991, 32, 2807; Ru: (m) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J Am Chem Soc 1989, 111, 5954; for a recent review article: (n) Murahashi, S.-I.; Takaya, H. Acc Chem Res 2000, 33, 225; For Mannich-type reactions: Ni, Rh, Pd: (o) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J Am Chem Soc 1994, 116, 3161; for other reactions (p) Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J Org Chem 1971, 36, 3316; (q) Ito, Y.; Nakatsuka, M.; Saegusa, T. J Org Chem 1980, 45, 2022; (r) Ito, Y.; Konoike, T.; Saegusa, T. J Am Chem Soc 1975, 97, 649; Au: (s) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett 1996, 37, 4969.
41. (a) Ito, Y.; Sawamura, M.; Hayashi, T. J Am Chem Soc 1986, 108, 6405;
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43. (a) Carreira, E. M. In Comprehensive Asymmetric Catalysis. E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Eds. Springer: Berlin, 1999; Vol. 3, Chapter 29.1;
44. (b) Carreira, E. M. In Catalytic Asymmetric Synthesis, 2nd ed. I. Ojima Ed. Wiley: New York, 2000; Chapter 8B2.
45. For examples of acceleration in the transmetallation step with oxygen nucleophiles: (a) Miyaura, N.; Suzuki, A. Chem Rev 1995, 95, 2457; (b) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J Am Chem Soc 2002, 124, 5052.
46. For examples of acceleration in the transmetallation step with oxygen nucleophiles: (a) Miyaura, N.; Suzuki, A. Chem Rev 1995, 95, 2457; (b) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J Am Chem Soc 2002, 124, 5052.
47. Cu: (a) Krüger, J.; Carreira, E. M. J Am Chem Soc 1998, 120, 837; Pt: (b) Fujimura, O. J Am Chem Soc 1998, 120, 10032; Rh (c) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J Am Chem Soc 2000, 122, 4528.
48. Cu: (a) Krüger, J.; Carreira, E. M. J Am Chem Soc 1998, 120, 837; Pt: (b) Fujimura, O. J Am Chem Soc 1998, 120, 10032; Rh (c) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J Am Chem Soc 2000, 122, 4528.
49. Cu: (a) Krüger, J.; Carreira, E. M. J Am Chem Soc 1998, 120, 837; Pt: (b) Fujimura, O. J Am Chem Soc 1998, 120, 10032; Rh (c) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J Am Chem Soc 2000, 122, 4528.
50. (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J Am Chem Soc 1998, 120, 2474;
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