Rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds: Large accelerating effects of bases and ligands

Journal of Organic Chemistry

Volumn 68, Issue 15, 2003, Pages 6000-6004

  Itooka, Ryoh ^a   Iguchi, Yuki ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MILD CONDITIONS;

ADDITION REACTIONS; ALDEHYDES; CATALYST ACTIVITY; DERIVATIVES; ESTERS; KETONES; RHODIUM; UNSATURATED COMPOUNDS;

ORGANIC ACIDS;

1,5 CYCLOOCTADIENE LIGAND; ALDEHYDE; ALKADIENE; ALPHA,BETA UNSATURATED CARBONYL DERIVATIVE; AMIDE; BASE; BORONIC ACID DERIVATIVE; CARBONYL DERIVATIVE; ESTER; HYDROXO LIGAND; KETONE; LIGAND; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM HYDROXIDE; RHODIUM; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; LOW TEMPERATURE; REACTION ANALYSIS;

EID: 0038034717     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0207067     Document Type: Article

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31. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
32. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
33. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
34. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
35. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
36. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
37. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
38. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
39. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
40. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
41. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
42. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
43. Asymmetric 1,4-addition of B to enones: (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052. (b) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (d) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (e) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921. (f) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (g) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716. (i) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999,121, 11591. (j) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047. (k) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957. (l) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479. (m) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For reviews, see: (n) Hayashi, T. Synlett 2001, 879. (o) Miyaura, N. In Organoboranes for Synthses; ACS Symp. Ser. 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; pp 94-107.
44. Addition of B to alkenes and alkynes: (a) Lautenes, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311. (b) Murakami, M.; Igawa, H. J. Chem. Soc., Chem. Commun. 2002, 390. (c) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (d) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (f) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
45. Addition of B to alkenes and alkynes: (a) Lautenes, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311. (b) Murakami, M.; Igawa, H. J. Chem. Soc., Chem. Commun. 2002, 390. (c) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (d) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (f) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
46. Addition of B to alkenes and alkynes: (a) Lautenes, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311. (b) Murakami, M.; Igawa, H. J. Chem. Soc., Chem. Commun. 2002, 390. (c) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (d) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (f) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
47. Addition of B to alkenes and alkynes: (a) Lautenes, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311. (b) Murakami, M.; Igawa, H. J. Chem. Soc., Chem. Commun. 2002, 390. (c) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (d) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (f) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
48. Addition of B to alkenes and alkynes: (a) Lautenes, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311. (b) Murakami, M.; Igawa, H. J. Chem. Soc., Chem. Commun. 2002, 390. (c) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (d) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (f) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
49. Addition of B to alkenes and alkynes: (a) Lautenes, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311. (b) Murakami, M.; Igawa, H. J. Chem. Soc., Chem. Commun. 2002, 390. (c) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (d) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (e) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (f) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
50. Addition of Si to enones and alkynes: (a) Murata, M.; Shimazaki, R.; Ishikura, M.; Watanabe, S.; Masuda, Y. Synthesis 2002, 717. (b) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 295. (c) Koike, T.; Du, X.; Mori, A.; Osakada, K. Synlett 2002, 301. (d) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 667. (e) Huang, T.-S.; Li, C.-J. J. Chem. Soc., Chem. Commun. 2001, 2348.
51. Addition of Si to enones and alkynes: (a) Murata, M.; Shimazaki, R.; Ishikura, M.; Watanabe, S.; Masuda, Y. Synthesis 2002, 717. (b) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 295. (c) Koike, T.; Du, X.; Mori, A.; Osakada, K. Synlett 2002, 301. (d) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 667. (e) Huang, T.-S.; Li, C.-J. J. Chem. Soc., Chem. Commun. 2001, 2348.
52. Addition of Si to enones and alkynes: (a) Murata, M.; Shimazaki, R.; Ishikura, M.; Watanabe, S.; Masuda, Y. Synthesis 2002, 717. (b) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 295. (c) Koike, T.; Du, X.; Mori, A.; Osakada, K. Synlett 2002, 301. (d) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 667. (e) Huang, T.-S.; Li, C.-J. J. Chem. Soc., Chem. Commun. 2001, 2348.
53. Addition of Si to enones and alkynes: (a) Murata, M.; Shimazaki, R.; Ishikura, M.; Watanabe, S.; Masuda, Y. Synthesis 2002, 717. (b) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 295. (c) Koike, T.; Du, X.; Mori, A.; Osakada, K. Synlett 2002, 301. (d) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 667. (e) Huang, T.-S.; Li, C.-J. J. Chem. Soc., Chem. Commun. 2001, 2348.
54. Addition of Si to enones and alkynes: (a) Murata, M.; Shimazaki, R.; Ishikura, M.; Watanabe, S.; Masuda, Y. Synthesis 2002, 717. (b) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 295. (c) Koike, T.; Du, X.; Mori, A.; Osakada, K. Synlett 2002, 301. (d) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 667. (e) Huang, T.-S.; Li, C.-J. J. Chem. Soc., Chem. Commun. 2001, 2348.
55. Addition of Si to aldehydes: (a) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 298. (b) Oi, S.; Moro, M.; Inoue, Y. Organometallics 2001, 20, 1036. (c) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614.
56. Addition of Si to aldehydes: (a) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 298. (b) Oi, S.; Moro, M.; Inoue, Y. Organometallics 2001, 20, 1036. (c) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614.
57. Addition of Si to aldehydes: (a) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 298. (b) Oi, S.; Moro, M.; Inoue, Y. Organometallics 2001, 20, 1036. (c) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614.
58. Addition of Sn to enones: (a) Oi, S.; Moro, M.; Ito, H.; Honma, Y.; Miyano, S.; Inoue, Y. Tetrahedron 2002, 58, 91. (b) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (c) Oi, S.; Moro, M.; Ono, S.; Inoue, Y. Chem. Lett. 1998, 83.
59. Addition of Sn to enones: (a) Oi, S.; Moro, M.; Ito, H.; Honma, Y.; Miyano, S.; Inoue, Y. Tetrahedron 2002, 58, 91. (b) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (c) Oi, S.; Moro, M.; Ono, S.; Inoue, Y. Chem. Lett. 1998, 83.
60. Addition of Sn to enones: (a) Oi, S.; Moro, M.; Ito, H.; Honma, Y.; Miyano, S.; Inoue, Y. Tetrahedron 2002, 58, 91. (b) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (c) Oi, S.; Moro, M.; Ono, S.; Inoue, Y. Chem. Lett. 1998, 83.
61. Addition of Sn to aldehydes and imines: (a) Li, C.-J.; Meng, Y. J. Am. Chem. Soc. 2000, 122, 9538. (b) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. (c) Oi, S.; Moro, M.; Fukuhara, H.; Kawanishi, T.; Inoue, Y. Tetrahedron Lett. 1999, 40, 9259. (d) Oi, S.; Moro, M.; Inoue, Y. J. Chem. Soc., Chem. Commun. 1997, 1621.
62. Addition of Sn to aldehydes and imines: (a) Li, C.-J.; Meng, Y. J. Am. Chem. Soc. 2000, 122, 9538. (b) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. (c) Oi, S.; Moro, M.; Fukuhara, H.; Kawanishi, T.; Inoue, Y. Tetrahedron Lett. 1999, 40, 9259. (d) Oi, S.; Moro, M.; Inoue, Y. J. Chem. Soc., Chem. Commun. 1997, 1621.
63. Addition of Sn to aldehydes and imines: (a) Li, C.-J.; Meng, Y. J. Am. Chem. Soc. 2000, 122, 9538. (b) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. (c) Oi, S.; Moro, M.; Fukuhara, H.; Kawanishi, T.; Inoue, Y. Tetrahedron Lett. 1999, 40, 9259. (d) Oi, S.; Moro, M.; Inoue, Y. J. Chem. Soc., Chem. Commun. 1997, 1621.
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