Conjugate additions of a simple monosilylcopper reagent with use of the CuI-DMS complex: Stereoselectivities and a dramatic impact by DMS

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 580-589

  Dambacher, Jesse ^a   Bergdahl, Mikael ^a  

^a SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; OLIGOMERS; REACTION KINETICS; SOLVENTS;

DIMETHYL SULFIDE (DMS); MONOSILYLCOPPER REAGENT; OLIGOMERIZATION;

AROMATIC HYDROCARBONS;

3 (DIMETHYLPHENYLSILYL) 3 METHYLCYCLOHEXANONE; 3 (DIMETHYLPHENYLSILYL) 3 METHYLCYCLOPENTANONE; 3 (DIMETHYLPHENYLSILYL) 5 TRIMETHYLSILYLPENT 4 YNOIC ACID METHYL ESTER; 3 (DIMETHYLPHENYLSILYL)CYCLOPENTANONE; 3 (METHYLDIPHENYLSILYL)BUTANOIC ACID ETHYL ESTER; 4 (DIMETHYLPHENYLSILYL) 4 METHYL PENTAN 2 ONE; COPPER DERIVATIVE; DIALKYLZINC; DIMETHYL SULFIDE; ESTER DERIVATIVE; HEMPA; N (3'S DIMETHYLPHENYLSILYL 4' METHYLPENTANOYL) 4 PHENYL 1,3 OXAZOLIDIN 2 ONE; N (3'S HYDROXY 4' METHYLPENTANOYL) 4 PHENYL 1,3 OXAZOLIDIN 2 ONE; N (3'S HYDROXY 4' METHYLPENTANOYL) 4 TERT BUTYL 1,3 OXAZOLIDIN 2 ONE; N (3'S HYDROXYBUTANOYL) 5 DIPHENYL TERT BUTYLSILYL OXYMETHYL 2 PYRROLIDINONE; OXAZOLIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SILYLCYANOCUPRATE; TRIBUTYLPHOSPHINE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CONJUGATION; ENANTIOMER; OLIGOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 12344264557     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048269e     Document Type: Article

References (104)

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15. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
16. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
17. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
18. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
19. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
20. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
21. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
22. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
23. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
24. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
25. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
26. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
27. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
28. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
29. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
30. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
31. Reviews on asymmetric acetate aldol reactions, see: (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30. (b) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24-37. Articles on auxiliary based asymmetric acetate aldol reactions, see: (c) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439-2442. (d) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874-875. (e) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397-6400. (f) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180-182. Articles on chiral metal complexes in acetate aldol reactions, see: (g) Masamune, S.; Sato, T.; Kim, B.-M.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281. (h) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 495-497. (i) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. Articles on tin-enolates in acetate aldol reactions, see: (j) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418-1419. (k) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2391-2393. Articles on lithium-enolates in acetate aldol reactions, see: (l) Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034. (m) Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406. (n) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. 1998, 37, 3378-3381. Articles on boron-enolates in acetate aldol reactions, see: (o) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S. J. Org. Chem. 1994, 59, 8187-8191. (p) Zhang, Y.; Phillips, A. J.; Sammakia, T. Org. Lett. 2004, 6, 23-25. Articles on titanium-enolates in acetate aldol reactions, see: (q) Yan, T.-H.; Hung, A.-W.; Lee, H.-C.; Chang, C.-S.;, Liu, W.-H. J. Org. Chem. 1995, 60, 3301-3306. (r) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949-8952. (s) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-2256. (t) Hodge, M. B.; Olivo, H. F. Tetrahedron 2004, 60, 9397-9403.
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