Asymmetric synthesis of β-amino carbonyl compounds with N-sulfinyl β-amino Weinreb amides

Journal of Organic Chemistry

Volumn 70, Issue 6, 2005, Pages 2184-2190

  Davis, Franklin A ^a   Nolt, M Brad ^a   Wu, Yongzhong ^a   Prasad, Kavirayani R ^a,b   Li, Danyang ^a   Yang, Bin ^a   Bowen, Kerisha ^a   Lee, Seung H ^a   Eardley, John H ^a  

^a Temple University   (United States)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN COMPOUNDS; ORGANOMETALLICS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

Β-AMINO CARBONYL COMPOUNDS; Β-AMINO WEINREB AMIDES; ASYMMETRIC SYNTHESIS; NATURAL PRODUCTS;

ESTERS;

ACETAMIDE DERIVATIVE; AMIDE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; HYDROXYLAMINE; IMINE; ORGANOMETALLIC COMPOUND; POTASSIUM;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY;

ALDEHYDES; AMIDES; KETONES; MOLECULAR CONFORMATION; STEREOISOMERISM; SULFOXIDES;

EID: 15444381133     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0402780     Document Type: Article

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16. Asymmetric syntheses of β-amino aldehydes and ketones: (a) reduction of β-amino esters, or nitriles: refs 5 and 9 of this article and: Davis, F. A.; Szewczyk J. M. Tetrahedron Lett. 1898, 39, 5951. (b) Addition of methyl ketone enolates to sulfinimines, see ref 10. (c) Oxidation of γ-amino alcohols, see: Davies, S. B.; McKervey, M. A. Tetrahedron Lett. 1999, 40, 1229. (d) Arndt-Eistert reaction: (i) Rodriguez, M.; Aumelas, A.; Martinez, J. Tetrahedron Lett. 1990, 31, 5153. (ii) Rodriguez, M.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1980, 31, 7319. (iii) Limal, D.; Quesnel, A.; Briand, J.-P. Tetrahedron Lett. 1898, 39, 4239. (e) Hydrolysis of 1,3-oxazines, see: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. (f) Rearrangement of 2,3-aziridinio alcohols, see: Wang, B. M.; Song, Z. L.; Fan, C. A.; Tu, Y. Q.; Shi, Y. Org. Lett. 2002, 4, 363.
17. Asymmetric syntheses of β-amino aldehydes and ketones: (a) reduction of β-amino esters, or nitriles: refs 5 and 9 of this article and: Davis, F. A.; Szewczyk J. M. Tetrahedron Lett. 1898, 39, 5951. (b) Addition of methyl ketone enolates to sulfinimines, see ref 10. (c) Oxidation of γ-amino alcohols, see: Davies, S. B.; McKervey, M. A. Tetrahedron Lett. 1999, 40, 1229. (d) Arndt-Eistert reaction: (i) Rodriguez, M.; Aumelas, A.; Martinez, J. Tetrahedron Lett. 1990, 31, 5153. (ii) Rodriguez, M.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1980, 31, 7319. (iii) Limal, D.; Quesnel, A.; Briand, J.-P. Tetrahedron Lett. 1898, 39, 4239. (e) Hydrolysis of 1,3-oxazines, see: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. (f) Rearrangement of 2,3-aziridinio alcohols, see: Wang, B. M.; Song, Z. L.; Fan, C. A.; Tu, Y. Q.; Shi, Y. Org. Lett. 2002, 4, 363.
18. Asymmetric syntheses of β-amino aldehydes and ketones: (a) reduction of β-amino esters, or nitriles: refs 5 and 9 of this article and: Davis, F. A.; Szewczyk J. M. Tetrahedron Lett. 1898, 39, 5951. (b) Addition of methyl ketone enolates to sulfinimines, see ref 10. (c) Oxidation of γ-amino alcohols, see: Davies, S. B.; McKervey, M. A. Tetrahedron Lett. 1999, 40, 1229. (d) Arndt-Eistert reaction: (i) Rodriguez, M.; Aumelas, A.; Martinez, J. Tetrahedron Lett. 1990, 31, 5153. (ii) Rodriguez, M.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1980, 31, 7319. (iii) Limal, D.; Quesnel, A.; Briand, J.-P. Tetrahedron Lett. 1898, 39, 4239. (e) Hydrolysis of 1,3-oxazines, see: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. (f) Rearrangement of 2,3-aziridinio alcohols, see: Wang, B. M.; Song, Z. L.; Fan, C. A.; Tu, Y. Q.; Shi, Y. Org. Lett. 2002, 4, 363.
19. Asymmetric syntheses of β-amino aldehydes and ketones: (a) reduction of β-amino esters, or nitriles: refs 5 and 9 of this article and: Davis, F. A.; Szewczyk J. M. Tetrahedron Lett. 1898, 39, 5951. (b) Addition of methyl ketone enolates to sulfinimines, see ref 10. (c) Oxidation of γ-amino alcohols, see: Davies, S. B.; McKervey, M. A. Tetrahedron Lett. 1999, 40, 1229. (d) Arndt-Eistert reaction: (i) Rodriguez, M.; Aumelas, A.; Martinez, J. Tetrahedron Lett. 1990, 31, 5153. (ii) Rodriguez, M.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1980, 31, 7319. (iii) Limal, D.; Quesnel, A.; Briand, J.-P. Tetrahedron Lett. 1898, 39, 4239. (e) Hydrolysis of 1,3-oxazines, see: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. (f) Rearrangement of 2,3-aziridinio alcohols, see: Wang, B. M.; Song, Z. L.; Fan, C. A.; Tu, Y. Q.; Shi, Y. Org. Lett. 2002, 4, 363.
20. Asymmetric syntheses of β-amino aldehydes and ketones: (a) reduction of β-amino esters, or nitriles: refs 5 and 9 of this article and: Davis, F. A.; Szewczyk J. M. Tetrahedron Lett. 1898, 39, 5951. (b) Addition of methyl ketone enolates to sulfinimines, see ref 10. (c) Oxidation of γ-amino alcohols, see: Davies, S. B.; McKervey, M. A. Tetrahedron Lett. 1999, 40, 1229. (d) Arndt-Eistert reaction: (i) Rodriguez, M.; Aumelas, A.; Martinez, J. Tetrahedron Lett. 1990, 31, 5153. (ii) Rodriguez, M.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1980, 31, 7319. (iii) Limal, D.; Quesnel, A.; Briand, J.-P. Tetrahedron Lett. 1898, 39, 4239. (e) Hydrolysis of 1,3-oxazines, see: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. (f) Rearrangement of 2,3-aziridinio alcohols, see: Wang, B. M.; Song, Z. L.; Fan, C. A.; Tu, Y. Q.; Shi, Y. Org. Lett. 2002, 4, 363.
21. Asymmetric syntheses of β-amino aldehydes and ketones: (a) reduction of β-amino esters, or nitriles: refs 5 and 9 of this article and: Davis, F. A.; Szewczyk J. M. Tetrahedron Lett. 1898, 39, 5951. (b) Addition of methyl ketone enolates to sulfinimines, see ref 10. (c) Oxidation of γ-amino alcohols, see: Davies, S. B.; McKervey, M. A. Tetrahedron Lett. 1999, 40, 1229. (d) Arndt-Eistert reaction: (i) Rodriguez, M.; Aumelas, A.; Martinez, J. Tetrahedron Lett. 1990, 31, 5153. (ii) Rodriguez, M.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1980, 31, 7319. (iii) Limal, D.; Quesnel, A.; Briand, J.-P. Tetrahedron Lett. 1898, 39, 4239. (e) Hydrolysis of 1,3-oxazines, see: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. (f) Rearrangement of 2,3-aziridinio alcohols, see: Wang, B. M.; Song, Z. L.; Fan, C. A.; Tu, Y. Q.; Shi, Y. Org. Lett. 2002, 4, 363.
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29. For reviews on the chemistry of sulfinimines see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M , Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003.
30. For reviews on the chemistry of sulfinimines see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M , Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003.
31. For reviews on the chemistry of sulfinimines see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. In Advances in Sulfur Chemistry; Rayner, C. M , Ed.; JAI Press: Stamford, CT, 2000; Vol. 2, pp 249-282. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003.
32. For a preliminary account of this work see ref 6 of this article.
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35. For references to the application of N-sulfinyl δ-amino β-keto esters for the asymmetric synthesis of piperidine derivatives see: (a) Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041. (b) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Zhang, Y.; Anilkumar, G. J. Org. Chem. 2003, 68, 8061. (f) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
36. For references to the application of N-sulfinyl δ-amino β-keto esters for the asymmetric synthesis of piperidine derivatives see: (a) Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041. (b) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Zhang, Y.; Anilkumar, G. J. Org. Chem. 2003, 68, 8061. (f) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
37. For references to the application of N-sulfinyl δ-amino β-keto esters for the asymmetric synthesis of piperidine derivatives see: (a) Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041. (b) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623. (c) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 2106. (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169. (e) Davis, F. A.; Zhang, Y.; Anilkumar, G. J. Org. Chem. 2003, 68, 8061. (f) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
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