Acceleration of nucleophilic addition to vinylphosphonates and vinyl phosphine oxides by chlorotrimethylsilane

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7419-7422

  Afarinkia, Kamyar ^a   Binch, Hayley M ^a   Modi, Chetna ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE OXIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG; VINYLPHOSPHONATE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONJUGATION; STOICHIOMETRY; SYNTHESIS;

EID: 0032191514     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01612-8     Document Type: Article

References (18)

1. 1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992. Lee, V. J. in Comprehensive Organic Synthesis, Ed by Trost, B. M. and Fleming, I, Pergamon, Oxford, 1991, Vol 4. Schmaltz, H.-G. in Comprehensive Organic Synthesis, Ed by Trost, B. M. and Fleming, I, Pergamon, Oxford, 1991, Vol 4. For a review on asymmetric conjugate additions see: Rossiter, B. E. Swingle, N. M. Chem. Rev. 1992, 92, 771.
2. 1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992. Lee, V. J. in Comprehensive Organic Synthesis, Ed by Trost, B. M. and Fleming, I, Pergamon, Oxford, 1991, Vol 4. Schmaltz, H.-G. in Comprehensive Organic Synthesis, Ed by Trost, B. M. and Fleming, I, Pergamon, Oxford, 1991, Vol 4. For a review on asymmetric conjugate additions see: Rossiter, B. E. Swingle, N. M. Chem. Rev. 1992, 92, 771.
3. 1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992. Lee, V. J. in Comprehensive Organic Synthesis, Ed by Trost, B. M. and Fleming, I, Pergamon, Oxford, 1991, Vol 4. Schmaltz, H.-G. in Comprehensive Organic Synthesis, Ed by Trost, B. M. and Fleming, I, Pergamon, Oxford, 1991, Vol 4. For a review on asymmetric conjugate additions see: Rossiter, B. E. Swingle, N. M. Chem. Rev. 1992, 92, 771.
4. 1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992. Lee, V. J. in Comprehensive Organic Synthesis, Ed by Trost, B. M. and Fleming, I, Pergamon, Oxford, 1991, Vol 4. Schmaltz, H.-G. in Comprehensive Organic Synthesis, Ed by Trost, B. M. and Fleming, I, Pergamon, Oxford, 1991, Vol 4. For a review on asymmetric conjugate additions see: Rossiter, B. E. Swingle, N. M. Chem. Rev. 1992, 92, 771.
5. 2. Baldwin, I. C.; Beckett, R. P.; Williams, J. M. J. Synthesis 1996, 34-36.
6. 3. Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 3368-3370. Reetz, M. T.; Kindler, A. J. Chem. Soc., Chem. Commun. 1994, 2509-2510. Wipf, P.; Venkatraman, S.; J. Org. Chem. 1993, 58, 3455-3459.
7. 3. Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 3368-3370. Reetz, M. T.; Kindler, A. J. Chem. Soc., Chem. Commun. 1994, 2509-2510. Wipf, P.; Venkatraman, S.; J. Org. Chem. 1993, 58, 3455-3459.
8. 3. Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 3368-3370. Reetz, M. T.; Kindler, A. J. Chem. Soc., Chem. Commun. 1994, 2509-2510. Wipf, P.; Venkatraman, S.; J. Org. Chem. 1993, 58, 3455-3459.
9. 4. For the role of TMSCl in activation of C=O see: Horiguchi, Y.; Komatsu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087-7090. Bertz, S. H.; Miao, G., Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995,117, 11023-11024. For the role of TMSCl in d-π* stablisation between copper and an enone see: Corey, E. J.; Boaz N. W. Tetrahedron Lett. 1985, 26, 6015-6018. For a confluent postulate see: Lipshutz, B. H.; Dimock, S. H.; James, B. J. Am. Chem. Soc. 1993, 115, 9283-9284.
10. 4. For the role of TMSCl in activation of C=O see: Horiguchi, Y.; Komatsu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087-7090. Bertz, S. H.; Miao, G., Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995,117, 11023-11024. For the role of TMSCl in d-π* stablisation between copper and an enone see: Corey, E. J.; Boaz N. W. Tetrahedron Lett. 1985, 26, 6015-6018. For a confluent postulate see: Lipshutz, B. H.; Dimock, S. H.; James, B. J. Am. Chem. Soc. 1993, 115, 9283-9284.
11. 4. For the role of TMSCl in activation of C=O see: Horiguchi, Y.; Komatsu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087-7090. Bertz, S. H.; Miao, G., Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995,117, 11023-11024. For the role of TMSCl in d-π* stablisation between copper and an enone see: Corey, E. J.; Boaz N. W. Tetrahedron Lett. 1985, 26, 6015-6018. For a confluent postulate see: Lipshutz, B. H.; Dimock, S. H.; James, B. J. Am. Chem. Soc. 1993, 115, 9283-9284.
12. 4. For the role of TMSCl in activation of C=O see: Horiguchi, Y.; Komatsu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087-7090. Bertz, S. H.; Miao, G., Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995,117, 11023-11024. For the role of TMSCl in d-π* stablisation between copper and an enone see: Corey, E. J.; Boaz N. W. Tetrahedron Lett. 1985, 26, 6015-6018. For a confluent postulate see: Lipshutz, B. H.; Dimock, S. H.; James, B. J. Am. Chem. Soc. 1993, 115, 9283-9284.
13. 5. Kiddle, J. J.; Babler, J. H. J. Org. Chem. 1993, 58, 3572-3574. Savignac, P.; Teulade, M. P.; Aboujaoude, E. E.; Collignon, N. Synth. Commun. 1987, 17, 1559-1569. For a review see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333-349.
14. 5. Kiddle, J. J.; Babler, J. H. J. Org. Chem. 1993, 58, 3572-3574. Savignac, P.; Teulade, M. P.; Aboujaoude, E. E.; Collignon, N. Synth. Commun. 1987, 17, 1559-1569. For a review see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333-349.
15. 5. Kiddle, J. J.; Babler, J. H. J. Org. Chem. 1993, 58, 3572-3574. Savignac, P.; Teulade, M. P.; Aboujaoude, E. E.; Collignon, N. Synth. Commun. 1987, 17, 1559-1569. For a review see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333-349.
16. +) 258.1174, found 258.1165.
17. 7. Morrison, D. C. J. Am. Chem. Soc. 1950, 72, 4820-4821. See also: Buss, A. D.; Warren, S. J. Chem. Soc. Perkin Trans, 1 1985, 2307-2325.
18. 7. Morrison, D. C. J. Am. Chem. Soc. 1950, 72, 4820-4821. See also: Buss, A. D.; Warren, S. J. Chem. Soc. Perkin Trans, 1 1985, 2307-2325.