Imine allylations by allylic trichlorotins derived from α,α-diisopropylhomoallylic alcohols with tin(II) chloride and N-chlorosuccinimide

Synlett

Volumn , Issue 12, 2002, Pages 2113-2115

  Masuyama, Yoshiro ^a   Yamamoto, Naoko ^a   Kurusu, Yasuhiko ^a  

^a SOPHIA UNIVERSITY   (Japan)

Author keywords

Allylations; Allylic tins; Homoallylic amines; Nucleophilic additions; Organometallic reagents

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; AMINE; DICHLOROMETHANE; IMINE; ORGANOMETALLIC COMPOUND; SUCCINIMIDE DERIVATIVE; TIN CHLORIDE; TIN DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ADDITION REACTION; ALLYLATION; ARTICLE; LOW TEMPERATURE;

EID: 0036456098     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35581     Document Type: Article

References (27)

1. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
2. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
3. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
4. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
5. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
6. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
7. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
8. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
9. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
10. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
11. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
12. For recent non-Barbier-type imine allylations using imines, iminiums, oximes, hydrazones and so on, see: (a) Kise, N.; Yamazaki, H.; Mabuchi, T.; Shono, T. Tetrahedron Lett. 1994, 35, 1561. (b) Hoffman, R. V.; Nayar, N. K.; Shankweiler, J. M.; Klinekole, B. W. III Tetrahedron Lett. 1994, 35, 3231. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (d) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766. (e) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (f) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649. (g) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997. (h) Kobayashi, S.; Iwamoto, S.; Nagayama, S. Synlett 1997, 1099. (i) Billet, M.; Klotz, P.; Mann, A. Tetrahedron Lett. 2001, 42, 631. (j) Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 9493. (k) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
13. For Barbier-type imine allylations, see: (a) Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605. (b) Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589. (c) Vilaivan, T.; Winotapan, C.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2001, 42, 9073. (d) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563.
14. For Barbier-type imine allylations, see: (a) Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605. (b) Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589. (c) Vilaivan, T.; Winotapan, C.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2001, 42, 9073. (d) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563.
15. For Barbier-type imine allylations, see: (a) Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605. (b) Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589. (c) Vilaivan, T.; Winotapan, C.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2001, 42, 9073. (d) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563.
16. For Barbier-type imine allylations, see: (a) Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605. (b) Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589. (c) Vilaivan, T.; Winotapan, C.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2001, 42, 9073. (d) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563.
17. (a) Masuyama, Y. J. Synth. Org. Chem. Jpn. 1992, 50, 202. 9
18. (b) Masuyama, Y. In Advances in Metal-Organic Chemistry, Vol. 3; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1994, 255.
19. (c) Masuyama, Y. In Recent Research Developments in Organic Chemistry, Vol. 4; Transworld Research Network: Trivandrum, India, 2000, 373; and references cited therein.
20. The use of imines such as N-benzylideneaniline and N-benzylidenetosylamide in the allylation with tin(II) halides did not afford homoallylic amines but homoallylic alcohols in low yields.
21. Tin(II) chloride is insoluble in dichloromethane, and dissolves in dichloromethane containing an equimolar amount of alcohol to the tin(II) by adding an equimolar amount of NCS to the tin(II).
22. (a) Tagliavini, G. Rev. Silicon, Germanium, Tin, Lead 1985, 8, 237.
23. (b) Jones, P.; Knochel, P. J. Org. Chem. 1999, 64, 186; and references cited therein.
24. Masuyama, Y.; Saeki, K; Horiguchi, S.; Kurusu, Y. Synlett 2001, 1802.
25. Masuyama, Y.; Tosa, J.; Kurusu, Y. Chem. Commun. 1999, 1075.
26. 9 has been mistaken; syn adducts are major, similarly to the imine allylation by 5.
27. 8 the 2-butenyltrichlorotin intermediate is presumed to be an E,Z mixture.