A pyridylsilyl group expands the scope of catalytic intermolecular Pauson-Khand reactions

Angewandte Chemie - International Edition

Volumn 41, Issue 18, 2002, Pages 3481-3484

  Itami, Kenichiro ^a   Mitsudo, Koichi ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alkenes; Alkynes; Cycloadditions; Homogeneous catalysis; Silanes

Indexed keywords

CATALYSIS; MOLECULAR STRUCTURE; OLEFINS;

REGIOSELECTIVE;

AROMATIC COMPOUNDS;

ALKENE DERIVATIVE; CYCLOPENTENONE; DIMETHYL (2 PYRIDYL)SILYL DERIVATIVE; PYRIDINE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYPERBARISM; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037119779     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20020916)41:18<3481::AID-ANIE3481>3.0.CO;2-X     Document Type: Article

References (67)

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3. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
4. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
5. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
6. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
7. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
8. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
9. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
10. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
11. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
12. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
13. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
14. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
15. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
16. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
17. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
18. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
19. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
20. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
21. Examples of catalytic intermolecular PKR: a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. I 1973, 977; b) D. C. Billington, Tetrahedron Lett. 1983, 24, 2905; c) V. Rautenstrauch, P. Mégard. J. Conesa, W. Küster, Angew. Chem. 1990, 102, 1441; Angew. Chem. Int. Ed. Engl. 1990, 29, 1413; d) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. E. Hwang, J. Am. Chem. Soc. 1994, 116, 8793; e) N. Y. Lee, Y. K. Chung, Tetrahedron Lett. 1996, 37, 3145; f) N. Jeong, S. H. Hwang, Y. W. Lee, J. S. Lim, J. Am. Chem. Soc. 1997, 119, 10549; g) T. Sugihara, M. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 10782; h) J. W. Kim, Y. K. Chung, Synthesis 1998, 142; i) T. Sugihara, M. Yamaguchi, Synlett 1998, 1384; j) T. Rajesh, M. Periasamy, Tetrahedron Lett. 1999, 40, 817; k) S. W. Kim, S. U. Son, S. I. Lee, T. Hyeon, Y. K. Chung, J. Am. Chem. Soc. 2000, 122, 1550; l) M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, K. Saigo, Angew. Chem. 2000, 112, 645; Angew. Chem. Int. Ed. 2000, 39, 631; m) N. Jeong, S. H. Hwang, Angew. Chem. 2000, 112, 650; Angew. Chem. Int. Ed. 2000, 39, 636; n) M. E. Krafft, L. V. R. Boñaga, Angew. Chem. 2000, 112, 3822; Angew. Chem. Int. Ed. 2000, 39, 3676; o) T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852.
22. M. E. Krafft, Tetrahedron Lett. 1988, 29, 999.
23. Review on directed chemical reactions: A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307.
24. In investigating the stoichiometric PKR, several groups have exploited the directing group strategy for controlling the regio- and stereoselectivity. For example, see a) M. E. Krafft, C. A. Juliano, I. L. Scott, C. Wright, M. D. McEachin, J. Am. Chem. Soc. 1991, 113, 1693; b) S. Fonquerna, A. Moyano, M. A. Pericàs, A. Riera, J. Am. Chem. Soc. 1997, 119, 10225.
25. In investigating the stoichiometric PKR, several groups have exploited the directing group strategy for controlling the regio- and stereoselectivity. For example, see a) M. E. Krafft, C. A. Juliano, I. L. Scott, C. Wright, M. D. McEachin, J. Am. Chem. Soc. 1991, 113, 1693; b) S. Fonquerna, A. Moyano, M. A. Pericàs, A. Riera, J. Am. Chem. Soc. 1997, 119, 10225.
26. For the use of a removable directing group in metal-catalyzed reactions, see a) D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc. 1988, 110, 6917; b) B. Breit, Eur. J. Org. Chem. 1998, 1123; c) C. H. Jun, H. Lee, J. Am. Chem. Soc. 1999, 121, 880; d) N. D. Buezo, J. C. de la Rosa, J. Priego, I. Alonso, J. C. Carretero, Chem. Eur. J. 2001, 7, 3890; e) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750.
27. For the use of a removable directing group in metal-catalyzed reactions, see a) D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc. 1988, 110, 6917; b) B. Breit, Eur. J. Org. Chem. 1998, 1123; c) C. H. Jun, H. Lee, J. Am. Chem. Soc. 1999, 121, 880; d) N. D. Buezo, J. C. de la Rosa, J. Priego, I. Alonso, J. C. Carretero, Chem. Eur. J. 2001, 7, 3890; e) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750.
28. For the use of a removable directing group in metal-catalyzed reactions, see a) D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc. 1988, 110, 6917; b) B. Breit, Eur. J. Org. Chem. 1998, 1123; c) C. H. Jun, H. Lee, J. Am. Chem. Soc. 1999, 121, 880; d) N. D. Buezo, J. C. de la Rosa, J. Priego, I. Alonso, J. C. Carretero, Chem. Eur. J. 2001, 7, 3890; e) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750.
29. For the use of a removable directing group in metal-catalyzed reactions, see a) D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc. 1988, 110, 6917; b) B. Breit, Eur. J. Org. Chem. 1998, 1123; c) C. H. Jun, H. Lee, J. Am. Chem. Soc. 1999, 121, 880; d) N. D. Buezo, J. C. de la Rosa, J. Priego, I. Alonso, J. C. Carretero, Chem. Eur. J. 2001, 7, 3890; e) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750.
30. For the use of a removable directing group in metal-catalyzed reactions, see a) D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc. 1988, 110, 6917; b) B. Breit, Eur. J. Org. Chem. 1998, 1123; c) C. H. Jun, H. Lee, J. Am. Chem. Soc. 1999, 121, 880; d) N. D. Buezo, J. C. de la Rosa, J. Priego, I. Alonso, J. C. Carretero, Chem. Eur. J. 2001, 7, 3890; e) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750.
31. a) J. Yoshida, K. Itami, K. Mitsudo, S. Suga, Tetrahedron Lett. 1999, 40, 3403;
32. b) K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, J. Yoshida, J. Am. Chem. Soc. 2000, 122, 12013;
33. c) K. Itami, T. Nokami, J. Yoshida, J. Am. Chem. Soc. 2001, 123, 5600;
34. d) K. Itami, T. Koike, J. Yoshida, J. Am. Chem. Soc. 2001, 123, 6957;
35. e) K. Itami, T. Kamei, J. Yoshida, J. Am. Chem. Soc. 2001, 123, 8773;
36. f) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577;
37. g) K. Itami, K. Mitsudo, A. Nishino, J. Yoshida, Chem. Lett. 2001, 1088.
38. a) J. Yoshida, K. Itami, J. Synth. Org. Chem. Jpn. 2001, 59, 1086;
39. b) K. Itami, K. Mitsudo, T. Nokami, T. Kamei, T. Koike, J. Yoshida, J. Organomet. Chem. 2002, 653, 105.
40. a) M. Yamanaka, E. Nakamura, J. Am. Chem. Soc. 2001, 123, 1703;
41. b) F. Robert, A. Milet, Y. Gimbert, D. Konya, A. E. Greene, J. Am. Chem. Soc. 2001, 123, 5396;
42. c) T. J. M. de Bruin, A. Milet, F. Robert, Y. Gimbert, A. E. Greene, J. Am. Chem. Soc. 2001, 123, 7184.
43. K. Itami, K. Mitsudo, J. Yoshida, Angew. Chem. 2001, 113, 2399; Angew. Chem. Int. Ed. 2001, 40, 2337.
44. K. Itami, K. Mitsudo, J. Yoshida, Angew. Chem. 2001, 113, 2399; Angew. Chem. Int. Ed. 2001, 40, 2337.
45. a) K. Itami, K. Mitsudo, J. Yoshida, J. Org. Chem. 1999, 64, 8709 (oxidation);
46. b) ref. [7c] (Pd-catalyzed cross-coupling reaction);
47. c) ref. [7f] (protodesilylation);
48. d) K. Itami, T. Nokami, J. Yoshida, Tetrahedron 2001, 57, 5045 (electrophile-induced substitution reaction);
49. ref.[7e] (fluoride-catalyzed reaction with carbonyl compounds).
50. 8] also catalyzed this process albeit in lower yield.
51. 12] as a catalyst in the intramolecular PKR and related reactions, see a) T. Morimoto, N. Chatani, Y. Fukumoto, S. Murai, J. Org. Chem. 1997, 62, 3762; b) T. Kondo, N. Suzuki, T. Okada, T. Mitsudo, J. Am. Chem. Soc. 1997, 119, 6187; c) N. Chatani, T. Morimoto, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1998, 120, 5335; d) S. K. Kang, K. J. Kim, Y. T. Hong, Angew. Chem. 2002, 114, 1654; Angew. Chem. Int. Ed. 2002, 41, 1584.
52. 12] as a catalyst in the intramolecular PKR and related reactions, see a) T. Morimoto, N. Chatani, Y. Fukumoto, S. Murai, J. Org. Chem. 1997, 62, 3762; b) T. Kondo, N. Suzuki, T. Okada, T. Mitsudo, J. Am. Chem. Soc. 1997, 119, 6187; c) N. Chatani, T. Morimoto, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1998, 120, 5335; d) S. K. Kang, K. J. Kim, Y. T. Hong, Angew. Chem. 2002, 114, 1654; Angew. Chem. Int. Ed. 2002, 41, 1584.
53. 12] as a catalyst in the intramolecular PKR and related reactions, see a) T. Morimoto, N. Chatani, Y. Fukumoto, S. Murai, J. Org. Chem. 1997, 62, 3762; b) T. Kondo, N. Suzuki, T. Okada, T. Mitsudo, J. Am. Chem. Soc. 1997, 119, 6187; c) N. Chatani, T. Morimoto, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1998, 120, 5335; d) S. K. Kang, K. J. Kim, Y. T. Hong, Angew. Chem. 2002, 114, 1654; Angew. Chem. Int. Ed. 2002, 41, 1584.
54. 12] as a catalyst in the intramolecular PKR and related reactions, see a) T. Morimoto, N. Chatani, Y. Fukumoto, S. Murai, J. Org. Chem. 1997, 62, 3762; b) T. Kondo, N. Suzuki, T. Okada, T. Mitsudo, J. Am. Chem. Soc. 1997, 119, 6187; c) N. Chatani, T. Morimoto, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1998, 120, 5335; d) S. K. Kang, K. J. Kim, Y. T. Hong, Angew. Chem. 2002, 114, 1654; Angew. Chem. Int. Ed. 2002, 41, 1584.
55. 12] as a catalyst in the intramolecular PKR and related reactions, see a) T. Morimoto, N. Chatani, Y. Fukumoto, S. Murai, J. Org. Chem. 1997, 62, 3762; b) T. Kondo, N. Suzuki, T. Okada, T. Mitsudo, J. Am. Chem. Soc. 1997, 119, 6187; c) N. Chatani, T. Morimoto, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1998, 120, 5335; d) S. K. Kang, K. J. Kim, Y. T. Hong, Angew. Chem. 2002, 114, 1654; Angew. Chem. Int. Ed. 2002, 41, 1584.
56. [11d]
57. Very recently, we learned of the results from Pagenkopf and co-workers on the stoichiometric intramolecular PKR of silicon-tethered enynes, which include vinylsilane moieties: J. F. Reichwein, S. T. Iacono, M. C. Patel, B. L. Pagenkopf, Tetrahedron Lett. 2002, 43, 3739.
58. The development of nongaseous ethylene equivalents has been an active area of research. For example, see a) W. J. Kerr, M. McLaughlin, P. L. Pauson, S. M. Robertson, Chem. Commun. 1999, 2171; b) W. J. Kerr, M. McLaughlin, P. L. Pauson, S. M. Robertson, J. Organomet. Chem. 2001, 630, 104.
59. The development of nongaseous ethylene equivalents has been an active area of research. For example, see a) W. J. Kerr, M. McLaughlin, P. L. Pauson, S. M. Robertson, Chem. Commun. 1999, 2171; b) W. J. Kerr, M. McLaughlin, P. L. Pauson, S. M. Robertson, J. Organomet. Chem. 2001, 630, 104.
60. D. Huang, J. C. Huffman, J. C. Bollinger, O. Eisenstein, K. G. Caulton, J. Am. Chem. Soc. 1997, 119, 7398.
61. 2SiH: K. Itami, K. Mitsudo, A. Nishino, J. Yoshida, J. Org. Chem. 2002, 67, 2645.
62. G. Fráter, J. A. Bajgrowicz, P. Kraft, Tetrahedron 1998, 54, 7633, and references therein.
63. 6] complex and ethylene gas (35 atm): D. C. Billington, I. M. Helps, P. L. Pauson, W. Thomson, D. Willison, J. Organomet. Chem. 1988, 354, 233.
64. B. M. Trost, A. B. Pinkerton, J. Org. Chem. 2001, 66, 7714.
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