BF3-mediated additions of organolithiums to ketimines: X-ray crystal structures of BF3-ketimine complexes

Journal of Organic Chemistry

Volumn 70, Issue 6, 2005, Pages 2335-2337

  Ma, Yun ^a   Lobkovsky, Emil ^a   Collum, David B ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; COMPLEXATION; CONFORMATIONS; CRYSTAL STRUCTURE; NITROGEN COMPOUNDS; STEREOCHEMISTRY;

ALLYLIC STRAIN; KETIMINES; LITHIUM ACETYLIDES; ORGANOLITHIUMS;

ORGANOMETALLICS;

ALIPHATIC AMINE; ALLYL COMPOUND; BORON TRIFLUORIDE; ETHER; IMINE; ORGANOLITHIUM COMPOUND; BORANE DERIVATIVE; LITHIUM; ORGANOMETALLIC COMPOUND;

ADDITION REACTION; ARTICLE; COMPLEX FORMATION; CONFORMATION; CRYSTAL STRUCTURE; QUANTUM YIELD; STEREOCHEMISTRY; STEREOSPECIFICITY; X RAY; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BORANES; CRYSTALLOGRAPHY, X-RAY; IMINES; LITHIUM; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 15444365137     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0480895     Document Type: Article

References (35)

1. 3-mediated organolithium reactions see ref 2.
2. Aubrecht, K. B.; Winemiller, M. D.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 11084.
3. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
4. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
5. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
6. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
7. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
8. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
9. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
10. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
11. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
12. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
13. 3-mediated additions to aldimines: Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083. Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. Uno, H.; Okada, S.; Suzuki, H. Tetrahedron 1991, 47, 6231. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1982, 57, 1504. Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Campbell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. Meltz, C. N.; Volkmann, R. A. Tetrahedron Lett. 1983, 24, 4503. Alvaro, G.; Savoia, D. Synlett 2002, 651. Shimizu, M.; Niwa, Y.; Kawamoto, M. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1999, 41, 301 (CAN 132:308565 AN 1999:776438). Kawate, T.; Yamada, H.; Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776. Pyne, S. G.; Dikic, B.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1992, 45, 807.
14. 3-mediated additions of perfluoroalkyllithiums to aldimines and a single ketimine were reported: Uno, H.; Okada, S.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 7, 1165.
15. Reviews describing the organolithium chemistry of imines: Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, Y., Eds; Springer-Verlag: Heidelberg, Germany, 1999; Chapter 26.2. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Chapter 1.12. Bloch, R. Chem. Rev. 1998, 98, 1407.
16. Reviews describing the organolithium chemistry of imines: Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, Y., Eds; Springer-Verlag: Heidelberg, Germany, 1999; Chapter 26.2. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Chapter 1.12. Bloch, R. Chem. Rev. 1998, 98, 1407.
17. Reviews describing the organolithium chemistry of imines: Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, Y., Eds; Springer-Verlag: Heidelberg, Germany, 1999; Chapter 26.2. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Chapter 1.12. Bloch, R. Chem. Rev. 1998, 98, 1407.
18. Reviews describing the organolithium chemistry of imines: Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, Y., Eds; Springer-Verlag: Heidelberg, Germany, 1999; Chapter 26.2. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Chapter 1.12. Bloch, R. Chem. Rev. 1998, 98, 1407.
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21. 3-mediated reactions of organolithiums: (a) Eis, M. J.; Wrobel, J. E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693. (b) Brown, H. C.; Racherla, U. S.; Singh, S. M. Tetrahedron Lett. 1984, 25, 2411. (c) Davies, J. E.; Raithby, P. R.; Snaith, R.; Wheatley, A. E. H. J. Chem. Soc., Chem. Commun. 1997, 1797. (d) Barr, D.; Hutton, K. B.; Morris, J. H.; Mulvey, R. E.; Reed, D.; Snaith, R. J. Chem. Soc., Chem. Commun. 1986, 127.
22. 3-mediated reactions of organolithiums: (a) Eis, M. J.; Wrobel, J. E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693. (b) Brown, H. C.; Racherla, U. S.; Singh, S. M. Tetrahedron Lett. 1984, 25, 2411. (c) Davies, J. E.; Raithby, P. R.; Snaith, R.; Wheatley, A. E. H. J. Chem. Soc., Chem. Commun. 1997, 1797. (d) Barr, D.; Hutton, K. B.; Morris, J. H.; Mulvey, R. E.; Reed, D.; Snaith, R. J. Chem. Soc., Chem. Commun. 1986, 127.
23. 3-mediated reactions of organolithiums: (a) Eis, M. J.; Wrobel, J. E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693. (b) Brown, H. C.; Racherla, U. S.; Singh, S. M. Tetrahedron Lett. 1984, 25, 2411. (c) Davies, J. E.; Raithby, P. R.; Snaith, R.; Wheatley, A. E. H. J. Chem. Soc., Chem. Commun. 1997, 1797. (d) Barr, D.; Hutton, K. B.; Morris, J. H.; Mulvey, R. E.; Reed, D.; Snaith, R. J. Chem. Soc., Chem. Commun. 1986, 127.
24. Blackwell, J. M.; Piers, W. E.; Parvez, M.; McDonald, R. Organometallics 2002, 21, 1400.
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26. 3 complexes: Samuel, B.; Snaith, R.; Summerford, C.; Wade, K. J. Chem. Soc. A 1970, 2019.
27. Extensive leading references to the syn-anti isomerism in imines: Liao, S.; Collum, D. B. J. Am. Chem. Soc. 2003, 125, 15114.
28. 1H NMR spectrum of adduct 23 displayed an AB quartet for benzylic protons.
29. Leading references to nucleophilic additions to cyclohexanones: Lindsay, H. A.; Salisbury, C. L.; Cordes, W.; McIntosh, M. C. Org. Lett. 2001, 3, 4007. Yamataka, H. J. Phys. Org. Chem. 1995, 8, 445. Cieplak, A. S. Chem. Rev. 1989, 99, 1265.
30. Leading references to nucleophilic additions to cyclohexanones: Lindsay, H. A.; Salisbury, C. L.; Cordes, W.; McIntosh, M. C. Org. Lett. 2001, 3, 4007. Yamataka, H. J. Phys. Org. Chem. 1995, 8, 445. Cieplak, A. S. Chem. Rev. 1989, 99, 1265.
31. Leading references to nucleophilic additions to cyclohexanones: Lindsay, H. A.; Salisbury, C. L.; Cordes, W.; McIntosh, M. C. Org. Lett. 2001, 3, 4007. Yamataka, H. J. Phys. Org. Chem. 1995, 8, 445. Cieplak, A. S. Chem. Rev. 1989, 99, 1265.
32. For stereoselective reductions of imines and iminium salts in which allylic strain appears to be consequential, see: Hutchins, R. O.; Su, W. Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412. See also: Meza-Leon, R. L.; Crich, D.; Bernes, S.; Quintero, L. J. Org. Chem. 2004, 69, 3976.
33. For stereoselective reductions of imines and iminium salts in which allylic strain appears to be consequential, see: Hutchins, R. O.; Su, W. Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412. See also: Meza-Leon, R. L.; Crich, D.; Bernes, S.; Quintero, L. J. Org. Chem. 2004, 69, 3976.
34. n-Butyllithium can be recrystallized: Hoffmann, D.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 5810. Kottke, T.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 580.
35. n-Butyllithium can be recrystallized: Hoffmann, D.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 5810. Kottke, T.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 580.