Allylation of aldehydes catalyzed by chiral N,N′-bis(N-methyl-2- methylene-4,5-bisphenyl-imidazole)-1,2-cyclohexane diamine rhodium(III) complexes

Canadian Journal of Chemistry

Volumn 81, Issue 11, 2003, Pages 1206-1212

  LaRonde, Frank J ^a   Brook, Michael A ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

Aldehydes; Allylation; Enantioselectivity; Rhodium(III) tetramine complex

Indexed keywords

ALCOHOLS; CATALYSIS; CATALYSTS; RHODIUM COMPOUNDS;

ALLYLATION;

ALDEHYDES;

ALCOHOL DERIVATIVE; ALDEHYDE; ALLYLTRIBUTYLTIN; BUTYLTIN DERIVATIVE; IMIDAZOLE DERIVATIVE; N,N' BIS(N METHYL 2 METHYLENE 4,5 BISPHENYLIMIDAZOLE) 1,2 CYCLOHEXANEDIAMINE; POTASSIUM CARBONATE; REAGENT; RHODIUM COMPLEX; SILVER DERIVATIVE; SILVER TETRAFLUOROBORATE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; REDUCTION; SYNTHESIS;

EID: 1642494805     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v03-118     Document Type: Article

References (52)

1. Reviews: (a) R. Noyori. Asymmetric catalysts in organic synthesis. Wiley, New York. 1994; (b) H. Brunner and W. Zettlmeier. Handbook of enantioselective catalysis with transition metal compounds. Vol. I, II. VCH, Weinheim. 1993; (c) I. Ojima (Editor). Catalytic asymmetric synthesis. VCH, Weinheim. 1993; (d) E.N. Jacobsen, A. Pfaltz, and H. Yamamoto (Editors). Comprehensive asymmetric catalysis. Vol. I-III. Springer, Berlin. 1999.
2. Reviews: (a) R. Noyori. Asymmetric catalysts in organic synthesis. Wiley, New York. 1994; (b) H. Brunner and W. Zettlmeier. Handbook of enantioselective catalysis with transition metal compounds. Vol. I, II. VCH, Weinheim. 1993; (c) I. Ojima (Editor). Catalytic asymmetric synthesis. VCH, Weinheim. 1993; (d) E.N. Jacobsen, A. Pfaltz, and H. Yamamoto (Editors). Comprehensive asymmetric catalysis. Vol. I-III. Springer, Berlin. 1999.
3. Reviews: (a) R. Noyori. Asymmetric catalysts in organic synthesis. Wiley, New York. 1994; (b) H. Brunner and W. Zettlmeier. Handbook of enantioselective catalysis with transition metal compounds. Vol. I, II. VCH, Weinheim. 1993; (c) I. Ojima (Editor). Catalytic asymmetric synthesis. VCH, Weinheim. 1993; (d) E.N. Jacobsen, A. Pfaltz, and H. Yamamoto (Editors). Comprehensive asymmetric catalysis. Vol. I-III. Springer, Berlin. 1999.
4. Reviews: (a) R. Noyori. Asymmetric catalysts in organic synthesis. Wiley, New York. 1994; (b) H. Brunner and W. Zettlmeier. Handbook of enantioselective catalysis with transition metal compounds. Vol. I, II. VCH, Weinheim. 1993; (c) I. Ojima (Editor). Catalytic asymmetric synthesis. VCH, Weinheim. 1993; (d) E.N. Jacobsen, A. Pfaltz, and H. Yamamoto (Editors). Comprehensive asymmetric catalysis. Vol. I-III. Springer, Berlin. 1999.
5. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
6. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
7. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
8. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
9. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
10. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
11. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
12. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
13. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
14. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
15. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
16. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
17. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
18. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
19. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
20. Allylboranes: (a) H.C. Brown and P.K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983); (b) R.P. Short and S. Masamune. J. Am. Chem. Soc. 111, 1892 (1989) ; (c) U.S. Racherla and H.C. Brown. J. Org. Chem. 56, 401 (1991); Allylboronates: (d) T. Herol and R.W. Hoffman. Angew. Chem. Int. Ed. Engl. 17, 768 (1978); (e) A.E. Roush, A.S. Walts, and L.K. Hoong. J. Am. Chem. Soc. 107, 8186 (1985); (f) W.R. Roush, L.K. Hoong, M.A.J. Palmer, and J.C. Park. J. Org. Chem. 55, 4109 (1990); Allylboroadiazolidines: (g) E.J. Corey, C.-M. Yu, and S.S. Kim. J. Am. Chem. Soc. 111, 5495 (1989); Allyltitanates: (h) M. Riediker and R.O. Duthaler. Angew. Chem. Int. Ed. Engl. 28, 494 (1991); (i) B. Schmidt and D. Seebach. Angew. Chem. Int. Ed. Engl. 30, 99 (1991); (j) A. Hafner, R.O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992); Allylaluminum derivatives: (k) N. Minowa and T. Mukaiyama. Bull. Chem. Soc. Jpn. 60, 3697 (1987); Allylstannanes: (l) J. Otera, Y. Kawasaki, H. Mizuno, and Y. Shimizu. Chem. Lett. 1529 (1983); (m) J. Otera, Y Yoshinaga, T. Yamaji, T. Yoshioka, and Y. Kawasaki. Organometallics, 4, 1213 (1985); (n) G.P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Chem. Soc. Chem. Commun. 685 (1986); (o) G.P. Boldrini, L. Lodi, E. Tagliavini, C. Tarasco, C. Trombini, and A. Umani-Ronchi. J. Org. Chem. 52, 5447 (1987); Allylchromium complexes: (p) K. Sugimoto, S. Aoyagi, and C. Kibayashi. J. Org. Chem. 62, 2322 (1997).
21. (a) H. Yamamoto (Editor). Lewis acids in organic synthesis. Vol. 1, 2. Wiley-VCH Verlag GmbH, Weinheim. 2000;
22. (b) W.R. Roush. In Comprehensive organic synthesis. Vol. 2, 1. Edited by B.M. Trost, I. Fleming, and C.H. Heathcock. Pergamon, Oxford. 1991;
23. (c) Y. Yamamoto and N. Asao. Chem. Rev. 93, 2207 (1993);
24. (d) T. Bach. Angew. Chem. Int. Ed. Engl. 33, 417 (1994);
25. (e) A.H. Hoveyda and J.P. Morken. Angew. Chem. Int. Ed. Engl. 35, 1262 (1996).
26. (a) K. Furuta, M. Mouri, and H. Yamamoto. Synlett, 561 (1991);
27. (b) K. Ishihara, M. Mouri, Q. Gao, T. Maruyama, K. Furuta, and H. Yamamoto. J. Am. Chem. Soc. 115, 11 490 (1993).
28. (a) J.A. Marshall and Y. Tang. Synlett, 653 (1992);
29. (b) J.A. Marshall and M.R. Palovich. J. Org. Chem. 63, 4381 (1998).
30. (a) S. Aoki, K. Mikami, M. Terada, and T. Nakai. Tetrahedron, 49, 1783 (1993);
31. (b) A.L. Costa, M.G. Piazza, E. Tagliavini, C. Trombini, and A. Umani-Ronchi. J. Am. Chem. Soc. 115, 8467 (1993);
32. (c) G.E. Keck and D. Krishnamurthy. J. Org. Chem. 58, 6543 (1993);
33. (d) G.E. Keck, K.H. Tarbet, and L.S. Geraci. J. Am. Chem. Soc. 115, 8467 (1993);
34. (e) G.E. Keck and L.S. Geraci. Tetrahedron Lett. 34, 7827 (1993);
35. (f) S. Weigand and R. Rruckner. Chem. Eur. J. 2, 1077 (1996).
36. D.R. Gauthier, Jr. and E.M. Carreira. Angew. Chem. Int. Ed. Engl. 35, 2363 (1996).
37. (a) A. Yanagisawa, H. Nakashima, A. Ishiba, and H. Yamamoto. J. Am. Chem. Soc. 118, 4723 (1996);
38. (b) A. Yanagisawa, A. Ishiba, H. Nakashima, and H. Yamamoto. Synlett, 88 (1997).
39. (a) H. Nishiyama and Y. Motoyama. In Lewis acid chemistry: a practical approach. Edited by H. Yamamoto. Oxford University Press, Oxford, U.K. 1998. Chap 13;
40. (b) W. Odenkirk, A.L. Rheingold, and B. Bosnich. J. Am. Chem. Soc. 114, 6392 (1992);
41. (c) T.K. Hollis, W. Odenkirk, N.P. Robinson, J. Whelan, and B. Bosnich. Tetrahedron, 49, 5415 (1993).
42. (a) Y. Motoyama, H. Narusawa, and H. Nishiyama. Chem. Commun. 131 (1999);
43. (b) Y. Motoyama, M. Okano, H. Narusawa, N. Makihara, K. Aoki, and H. Nishiyama. Organometallics, 20, 1580 (2001).
44. M. Shi, G.-X. Lei, and Y. Masaki. Tetrahedron Asymmetry, 10, 2071 (1999).
45. F.J. LaRonde and M.A. Brook. Inorg. Chim. Acta, 296, 208 (1999).
46. (a) R.J. Sundberg and B. Martin. Chem. Rev. 74, 471 (1974);
47. (b) J.R. Aldrich-Wright, R.S. Vagg, P.A. Williams, and A. Peter. Coord. Chem. Rev. 166, 361 (1997);
48. (c) M.M. Aly. Rev. Inorg. Chem. 16, 315 (1996); 329 (1996).
49. (c) M.M. Aly. Rev. Inorg. Chem. 16, 315 (1996); 329 (1996).
50. Extracted from: F.J. LaRonde. Ph.D. thesis. McMaster University, Hamilton, Canada. 2000.
51. H. Nishiyama, M. Kondo, T. Nakamura, and K. Itoh. Organometallics, 10, 500 (1991).
52. J. Jacques, C.B. Gros, M.J. Brienne, and J. Toullec. Stereochemistry - fundamentals and methods, absolute configuration of 6000 selected compounds with one asymmetric carbon atom. Edited by H.B. Kagan. Georg Thieme Publishers, Stuttgart. 1977.