Asymmetric synthesis of homochiral Baylis-Hillman products employing (R)-N-methyl-N-α-methylbenzyl amide

Tetrahedron Asymmetry

Volumn 11, Issue 12, 2000, Pages 2437-2441

  Davies, Stephen G ^a   Smethurst, Christian A P ^a   Smith, Andrew D ^a   Smyth, G Darren ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; N METHYL N ALPHA METHYLBENZYL AMIDE; REAGENT; TERT BUTYL CINNAMATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CONJUGATE; CONJUGATION; CONTROLLED STUDY; METHODOLOGY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034733512     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00224-X     Document Type: Article

References (28)

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2. Baylis,A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q; Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
3. Baylis,A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q; Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
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5. Janecki, T. Synth. Commun. 1993, 23, 641; Hoffmann, H. M. R.; Rabe, J. J. Org. Chem. 1985, 50, 3849; Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94; Daude, N. Eggert U. and Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun., 1988; 206; Bailey, M. Markó, I. E. Ollis W. D. and Rasmussen,P. R. Tetrahedron Lett., 1990, 31, 4509.
6. Janecki, T. Synth. Commun. 1993, 23, 641; Hoffmann, H. M. R.; Rabe, J. J. Org. Chem. 1985, 50, 3849; Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94; Daude, N. Eggert U. and Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun., 1988; 206; Bailey, M. Markó, I. E. Ollis W. D. and Rasmussen,P. R. Tetrahedron Lett., 1990, 31, 4509.
7. Janecki, T. Synth. Commun. 1993, 23, 641; Hoffmann, H. M. R.; Rabe, J. J. Org. Chem. 1985, 50, 3849; Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94; Daude, N. Eggert U. and Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun., 1988; 206; Bailey, M. Markó, I. E. Ollis W. D. and Rasmussen,P. R. Tetrahedron Lett., 1990, 31, 4509.
8. Janecki, T. Synth. Commun. 1993, 23, 641; Hoffmann, H. M. R.; Rabe, J. J. Org. Chem. 1985, 50, 3849; Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94; Daude, N. Eggert U. and Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun., 1988; 206; Bailey, M. Markó, I. E. Ollis W. D. and Rasmussen,P. R. Tetrahedron Lett., 1990, 31, 4509.
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11. Atkinson, R. S.; Fawcett, J.; Russell, D. R.; Williams, P. J. J. Chem. Soc., Chem. Commun. 1994, 2031; Bailey, M.; Markó, I. E.; Ollis, W. D. Tetrahedron Lett. 1991, 32, 2687; Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307; Brzezinski, L. J.; Rafel, S.; Leahy, J. W. Tetrahedron 1997, 53, 16423.
12. Atkinson, R. S.; Fawcett, J.; Russell, D. R.; Williams, P. J. J. Chem. Soc., Chem. Commun. 1994, 2031; Bailey, M.; Markó, I. E.; Ollis, W. D. Tetrahedron Lett. 1991, 32, 2687; Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307; Brzezinski, L. J.; Rafel, S.; Leahy, J. W. Tetrahedron 1997, 53, 16423.
13. Gilbert, A.; Heritage, T. W.; Isaacs, N. S. Tetrahedron: Asymmetry 1991, 2, 969; Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241; Kündig, E. P.; Xu, L. H.; Romanens, P.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 7049; Barrett, A. G. M.; Kamimura, A. J. Chem. Soc., Chem. Commun. 1995, 1755; Burgess, K.; Jennings, L. D. J. Org. Chem. 1990, 55, 1138.
14. Gilbert, A.; Heritage, T. W.; Isaacs, N. S. Tetrahedron: Asymmetry 1991, 2, 969; Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241; Kündig, E. P.; Xu, L. H.; Romanens, P.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 7049; Barrett, A. G. M.; Kamimura, A. J. Chem. Soc., Chem. Commun. 1995, 1755; Burgess, K.; Jennings, L. D. J. Org. Chem. 1990, 55, 1138.
15. Gilbert, A.; Heritage, T. W.; Isaacs, N. S. Tetrahedron: Asymmetry 1991, 2, 969; Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241; Kündig, E. P.; Xu, L. H.; Romanens, P.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 7049; Barrett, A. G. M.; Kamimura, A. J. Chem. Soc., Chem. Commun. 1995, 1755; Burgess, K.; Jennings, L. D. J. Org. Chem. 1990, 55, 1138.
16. Gilbert, A.; Heritage, T. W.; Isaacs, N. S. Tetrahedron: Asymmetry 1991, 2, 969; Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241; Kündig, E. P.; Xu, L. H.; Romanens, P.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 7049; Barrett, A. G. M.; Kamimura, A. J. Chem. Soc., Chem. Commun. 1995, 1755; Burgess, K.; Jennings, L. D. J. Org. Chem. 1990, 55, 1138.
17. Gilbert, A.; Heritage, T. W.; Isaacs, N. S. Tetrahedron: Asymmetry 1991, 2, 969; Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241; Kündig, E. P.; Xu, L. H.; Romanens, P.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 7049; Barrett, A. G. M.; Kamimura, A. J. Chem. Soc., Chem. Commun. 1995, 1755; Burgess, K.; Jennings, L. D. J. Org. Chem. 1990, 55, 1138.
18. Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc., 1997, 119, 4317.
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22. Davies, S. G.; Smyth, G. D. Tetrahedron: Asymmetry 1996, 7, 1001.
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25. Asao, N.; Tsukada, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1993, 1660.
26. This stereochemical assignment was also confirmed by single crystal X-ray structural analysis of 11 which was established relative to the known (R) stereochemistry of the α-methylbenzyl fragment. For an example of a similar approach to proof of stereochemistry of β-amino ester enolate aldol reactions, see: Asao, N.; Uyehara, T.; Yamamoto, Y. Tetrahedron 1990, 46, 4563.
27. Cope, A. C.; Pike, R. A.; Spencer, C. F. J. Am. Chem. Soc. 1953, 75, 3212; Cram, D. J.; Sahyun, M. R. V.;Knox, G. R. J. Am. Chem. Soc. 1962, 84, 1734.
28. Cope, A. C.; Pike, R. A.; Spencer, C. F. J. Am. Chem. Soc. 1953, 75, 3212; Cram, D. J.; Sahyun, M. R. V.;Knox, G. R. J. Am. Chem. Soc. 1962, 84, 1734.