Sterically congested tripodal phosphites: Conformational analysis, solid-state polymorphism, metal complexation, and application to the asymmetric hydrosilation of ketones

Inorganic Chemistry

Volumn 42, Issue 17, 2003, Pages 5097-5106

  Shum, Sai P ^a   Pastor, Stephen D ^a   DeBellis, Anthony D ^a   Odorisio, Paul A ^a   Burke, Lilibeth ^a   Clarke, Frank H ^a   Rihs, Grety ^a   Piatek, Bogdan ^a   Rodebaugh, Ronald K ^a  

^a CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ETHYL ESTER; ACETONE; ACETOPHENONE; KETONE; LIGAND; METAL COMPLEX; PHOSPHITE; RHODIUM; TOLUENE; TRIS[2,2',2'' TRIS[[2,4,8,10 TETRAKIS(1,1 DIMETHYLETHYL)DIBENZO[D,F][1,3,2]DIOXAPHOSPHEPIN 6 YL]OXY]ETHYL]AMINE; TRIS[2,2',2'' TRIS[[2,4,8,10 TETRAKIS(1,1 DIMETHYLETHYL)DIBENZO[D,F][1,3,2]DIOXAPHOSPHEPIN 6 YL]OXY]PROPYL]AMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHIRALITY; COMPLEX FORMATION; CONFORMATION; CRYSTALLIZATION; CRYSTALLOGRAPHY; ENANTIOMER; HYDROSILATION; SOLID STATE; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0042510143     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic030099l     Document Type: Article

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71. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
72. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
73. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
74. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
75. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
76. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
77. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
78. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
79. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
80. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
81. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
82. For an example of an asymmetric hydrosilation reaction using a chiral phosphite ligand. see: (a) Babin. J. E.: Whiteker, G. T. U.S. Patent 5,360,938; Chem. Abstr. 1995, 122, 186609. For recent work on catalytic hydrosilation reactions, see: (b) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995. (c) Heldmann, D. K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096. (d) Moreau, C.; Frost, C. G.; Murrer, B. Tetrahedron Lett. 1999, 40, 5617. (e) Bideau, F. L.; Henique, J.; Samuel, E.; Elschenbroich, C. Chem. Commun. (Cambridge) 1999, 1397. (f) Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640. (g) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877. (h) Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y. Tetrahedron Lett. 1999, 40, 1327. (i) Nagashima, H.; Suzuki, A.; Iura, T.; Ryu, K.; Matsubara, K. Organometallics 2000, 19, 3579. (j) Son, S. U.; Paik, S. J.; Chung, Y. K. J. Mol. Catal. A 2000, 151, 87. (k) Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 485. (l) Smith, A. R.; Bruno, J. W.; Pastor, S. D. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 479. (m) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 13, 659. (n) Jensen, J. F.; Sørensen. H. O.: Johannsen, M. J. Org. Chem. 2003, 68, 1258.
83. For an excellent review of this work, see: Halpern, J. Asymmetric Synthesis; Academic Press: New York, 1985; Vol. 5, Chapter 2.