A novel enantioselective (2Z)-alk-2-enylation of aldehydes via an allyl-transfer reaction from chiral allyl donors prepared from (+)-isomenthone

Organic Letters

Volumn 6, Issue 8, 2004, Pages 1261-1264

  Nokami, Junzo ^a   Nomiyama, Kenta ^a   Shafi, Siddiqi M ^a   Kataoka, Kazuhide ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENYL GROUP; ALLYL ALCOHOL; ALLYL COMPOUND; ISOMENTHONE; MAGNESIUM CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY;

EID: 2542429225     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0400140     Document Type: Article

References (69)

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21. Allylsilane with chiral auxiliary or catalyst: (p) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (q) Zhang, L. C.; Sakurai, H.; Kira, M. Chem. Lett. 1997, 129-130. (r) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946-948. (s) Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920-7921. (t) Duthaler, R. O.; Hafner, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 43-45.
22. Allylsilane with chiral auxiliary or catalyst: (p) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (q) Zhang, L. C.; Sakurai, H.; Kira, M. Chem. Lett. 1997, 129-130. (r) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946-948. (s) Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920-7921. (t) Duthaler, R. O.; Hafner, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 43-45.
23. Allylsilane with chiral auxiliary or catalyst: (p) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (q) Zhang, L. C.; Sakurai, H.; Kira, M. Chem. Lett. 1997, 129-130. (r) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946-948. (s) Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920-7921. (t) Duthaler, R. O.; Hafner, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 43-45.
24. Allylsilane with chiral auxiliary or catalyst: (p) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. (q) Zhang, L. C.; Sakurai, H.; Kira, M. Chem. Lett. 1997, 129-130. (r) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946-948. (s) Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920-7921. (t) Duthaler, R. O.; Hafner, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 43-45.
25. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
26. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
27. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
28. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
29. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
30. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
31. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
32. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
33. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
34. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
35. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
36. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
37. Allyltributyltin with chiral catalyst: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (b) Weigand, S.; Brückner, R. Chem. Eur. J. 1996, 2, 1077-1084. (c) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145-148. (d) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756. (e) Yu, C-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761-762. (f) Motoyama, Y.; Narusawa, H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131-132. (g) Doucet, H.; Santelli, M. Tetrahedron: Asymmetry 2000, 11, 4163-4169. (h) Loh, T.-P.; Zhou, I.-R. Tetrahedron Lett. 2000, 41, 5261-5264. (i) Brenna, E.; Scaramelli, L.; Serra, S. Synlett 2000, 357-358. (j) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (k) Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769. (l) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. (m) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
38. Excess allyltributyltin or tetraallyltin with chiral catalyst (allylation of ketones): (n) Casolari, S.; D'Addario, D.; Tagliavini, E. Org. Lett. 1999, 1, 1061-1063. (o) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem., Int. Ed. 2002, 41, 3697-3699.
39. Excess allyltributyltin or tetraallyltin with chiral catalyst (allylation of ketones): (n) Casolari, S.; D'Addario, D.; Tagliavini, E. Org. Lett. 1999, 1, 1061-1063. (o) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem., Int. Ed. 2002, 41, 3697-3699.
40. Allylsilane with chiral catalyst: (p) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363-2365. (q) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021-12022. (r) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536-6537. (s) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047-1049. (t) Malkov, A. V.; Dufková, L.; Farrugia, L.; Kocovsky, P. Angew. Chem., Int. Ed. 2003, 42, 3674-3677.
41. Allylsilane with chiral catalyst: (p) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363-2365. (q) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021-12022. (r) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536-6537. (s) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047-1049. (t) Malkov, A. V.; Dufková, L.; Farrugia, L.; Kocovsky, P. Angew. Chem., Int. Ed. 2003, 42, 3674-3677.
42. Allylsilane with chiral catalyst: (p) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363-2365. (q) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021-12022. (r) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536-6537. (s) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047-1049. (t) Malkov, A. V.; Dufková, L.; Farrugia, L.; Kocovsky, P. Angew. Chem., Int. Ed. 2003, 42, 3674-3677.
43. Allylsilane with chiral catalyst: (p) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363-2365. (q) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021-12022. (r) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536-6537. (s) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047-1049. (t) Malkov, A. V.; Dufková, L.; Farrugia, L.; Kocovsky, P. Angew. Chem., Int. Ed. 2003, 42, 3674-3677.
44. Allylsilane with chiral catalyst: (p) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363-2365. (q) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021-12022. (r) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536-6537. (s) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047-1049. (t) Malkov, A. V.; Dufková, L.; Farrugia, L.; Kocovsky, P. Angew. Chem., Int. Ed. 2003, 42, 3674-3677.
45. (II)[salen]- catalyst: (u) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 1999, 38, 3357-3359. (v) Suzuki, T.; Kinoshita, A.; Kawada, H.; Nakada, M. Synlett 2003, 570-572. (w) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140-1141.
46. (II)[salen]- catalyst: (u) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 1999, 38, 3357-3359. (v) Suzuki, T.; Kinoshita, A.; Kawada, H.; Nakada, M. Synlett 2003, 570-572. (w) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140-1141.
47. (II)[salen]- catalyst: (u) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 1999, 38, 3357-3359. (v) Suzuki, T.; Kinoshita, A.; Kawada, H.; Nakada, M. Synlett 2003, 570-572. (w) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140-1141.
48. Asymmetric 1-methylallylation and related reactions: By chiral catalyst with tributylcrotyltin: (a) Marshall, J. A.; Tang, Y. Synlett 1992, 653-654.
49. By chiral catalyst with crotylsilane: (b) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-582. (c) Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 3701-3703. (d) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783-1792. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i. J. Am. Chem. Soc. 1998, 120, 6419-6420. (g) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488-9489.
50. By chiral catalyst with crotylsilane: (b) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-582. (c) Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 3701-3703. (d) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783-1792. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i. J. Am. Chem. Soc. 1998, 120, 6419-6420. (g) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488-9489.
51. By chiral catalyst with crotylsilane: (b) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-582. (c) Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 3701-3703. (d) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783-1792. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i. J. Am. Chem. Soc. 1998, 120, 6419-6420. (g) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488-9489.
52. By chiral catalyst with crotylsilane: (b) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-582. (c) Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 3701-3703. (d) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783-1792. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i. J. Am. Chem. Soc. 1998, 120, 6419-6420. (g) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488-9489.
53. By chiral catalyst with crotylsilane: (b) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-582. (c) Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 3701-3703. (d) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783-1792. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i. J. Am. Chem. Soc. 1998, 120, 6419-6420. (g) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488-9489.
54. By chiral catalyst with crotylsilane: (b) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-582. (c) Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 3701-3703. (d) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783-1792. (e) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767-2770. (f) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i. J. Am. Chem. Soc. 1998, 120, 6419-6420. (g) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488-9489.
55. (II)[salen]-catalyst with crotyl bromide and metallic Mn: (h) Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2000, 39, 2327-2330.
56. Noncatalytic reaction by a stoichiometric amount of chiral B-crotylborane reagents: (i) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294-296. (j) Roush, W. R.; Ando, K.; Powers, D. B.; Halterman, R. L.; Palkowitz, A. D. Tetrahedron Lett. 1988, 29, 5579-5582. (k) Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831-4832. (l) Brown, H. C.; Jadhav, R. K. Tetrahedron Lett. 1984, 25, 1215-1218. (m) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294. (n) Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439. (o) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576. (p) Ref 2c.
57. Noncatalytic reaction by a stoichiometric amount of chiral B-crotylborane reagents: (i) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294-296. (j) Roush, W. R.; Ando, K.; Powers, D. B.; Halterman, R. L.; Palkowitz, A. D. Tetrahedron Lett. 1988, 29, 5579-5582. (k) Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831-4832. (l) Brown, H. C.; Jadhav, R. K. Tetrahedron Lett. 1984, 25, 1215-1218. (m) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294. (n) Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439. (o) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576. (p) Ref 2c.
58. Noncatalytic reaction by a stoichiometric amount of chiral B-crotylborane reagents: (i) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294-296. (j) Roush, W. R.; Ando, K.; Powers, D. B.; Halterman, R. L.; Palkowitz, A. D. Tetrahedron Lett. 1988, 29, 5579-5582. (k) Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831-4832. (l) Brown, H. C.; Jadhav, R. K. Tetrahedron Lett. 1984, 25, 1215-1218. (m) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294. (n) Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439. (o) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576. (p) Ref 2c.
59. Noncatalytic reaction by a stoichiometric amount of chiral B-crotylborane reagents: (i) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294-296. (j) Roush, W. R.; Ando, K.; Powers, D. B.; Halterman, R. L.; Palkowitz, A. D. Tetrahedron Lett. 1988, 29, 5579-5582. (k) Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831-4832. (l) Brown, H. C.; Jadhav, R. K. Tetrahedron Lett. 1984, 25, 1215-1218. (m) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294. (n) Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439. (o) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576. (p) Ref 2c.
60. Noncatalytic reaction by a stoichiometric amount of chiral B-crotylborane reagents: (i) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294-296. (j) Roush, W. R.; Ando, K.; Powers, D. B.; Halterman, R. L.; Palkowitz, A. D. Tetrahedron Lett. 1988, 29, 5579-5582. (k) Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831-4832. (l) Brown, H. C.; Jadhav, R. K. Tetrahedron Lett. 1984, 25, 1215-1218. (m) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294. (n) Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439. (o) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576. (p) Ref 2c.
61. Noncatalytic reaction by a stoichiometric amount of chiral B-crotylborane reagents: (i) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294-296. (j) Roush, W. R.; Ando, K.; Powers, D. B.; Halterman, R. L.; Palkowitz, A. D. Tetrahedron Lett. 1988, 29, 5579-5582. (k) Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831-4832. (l) Brown, H. C.; Jadhav, R. K. Tetrahedron Lett. 1984, 25, 1215-1218. (m) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294. (n) Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439. (o) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576. (p) Ref 2c.
62. Noncatalytic reaction by a stoichiometric amount of chiral B-crotylborane reagents: (i) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294-296. (j) Roush, W. R.; Ando, K.; Powers, D. B.; Halterman, R. L.; Palkowitz, A. D. Tetrahedron Lett. 1988, 29, 5579-5582. (k) Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831-4832. (l) Brown, H. C.; Jadhav, R. K. Tetrahedron Lett. 1984, 25, 1215-1218. (m) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294. (n) Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439. (o) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576. (p) Ref 2c.
63. Noncatalytic reaction by a stoichiometric amount of chiral B-crotylborane reagents: (i) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294-296. (j) Roush, W. R.; Ando, K.; Powers, D. B.; Halterman, R. L.; Palkowitz, A. D. Tetrahedron Lett. 1988, 29, 5579-5582. (k) Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831-4832. (l) Brown, H. C.; Jadhav, R. K. Tetrahedron Lett. 1984, 25, 1215-1218. (m) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294. (n) Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439. (o) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576. (p) Ref 2c.
64. By a stoichiometric amount of crotyltitanium complex with a chiral auxiliary: (q) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 3995-3998.
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