Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions: Synthesis of 3-Aryl-δ-lactones

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1963-1966

  Smitrovich, Jacqueline H ^a   Boice, Geneviève N ^a   Qu, Chuanxing ^a   DiMichele, Lisa ^a   Nelson, Todd D ^a   Huffman, Mark A ^a   Murry, Jerry ^a   McNamara, James ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EPHEDRINE; LACTONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; EPHEDRINE; INDICATORS AND REAGENTS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 0037198780     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0259847     Document Type: Article

References (39)

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23. While this work was in progress, Myers et al. reported the conjugate addition of the lithium enolate derived from pseudoephedrine α-fluoroacetamide to a nitroalkene and vinyl sulfoxide with modest selectivities and yields See: Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc. 2001, 123, 7207-7219.
24. This method determines selectivity at the 4-position only, as epimerization occurs upon lactonization. Determination of the diastereomeric ratios of the Michael adducts by NMR spectroscopy is hampered by the presence of rotamers.
25. For a review of the synthetic applications of cis-1-amino-2-indanol see: Senanayake, C. H. Aldrichimica Acta 1998, 31, 3-15.
26. Myers et al. have demonstrated the power of pseudoephedrine as a chiral auxiliary for enolate alkylations: (a) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322-3327. (b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. Myers, A. G.; Yoon, T. Tetrahedron Lett. 1995, 36, 9429-9432. (d) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488-8489. (e) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361-9362.
27. Myers et al. have demonstrated the power of pseudoephedrine as a chiral auxiliary for enolate alkylations: (a) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322-3327. (b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. Myers, A. G.; Yoon, T. Tetrahedron Lett. 1995, 36, 9429-9432. (d) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488-8489. (e) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361-9362.
28. Myers et al. have demonstrated the power of pseudoephedrine as a chiral auxiliary for enolate alkylations: (a) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322-3327. (b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. Myers, A. G.; Yoon, T. Tetrahedron Lett. 1995, 36, 9429-9432. (d) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488-8489. (e) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361-9362.
29. Myers et al. have demonstrated the power of pseudoephedrine as a chiral auxiliary for enolate alkylations: (a) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322-3327. (b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. Myers, A. G.; Yoon, T. Tetrahedron Lett. 1995, 36, 9429-9432. (d) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488-8489. (e) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361-9362.
30. Myers et al. have demonstrated the power of pseudoephedrine as a chiral auxiliary for enolate alkylations: (a) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322-3327. (b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. Myers, A. G.; Yoon, T. Tetrahedron Lett. 1995, 36, 9429-9432. (d) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488-8489. (e) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361-9362.
31. Myers et al. have demonstrated the power of pseudoephedrine as a chiral auxiliary for enolate alkylations: (a) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322-3327. (b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511. (c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673. Myers, A. G.; Yoon, T. Tetrahedron Lett. 1995, 36, 9429-9432. (d) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488-8489. (e) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361-9362.
32. (a) For use of pseudoephedrine as a chiral auxiliary for asymmetric aldol reaction see: Vicario, J. L.; Badía, D.; Domínguez, E.; Rodríguez, M.; Carrillo, L. J. Org. Chem. 2000, 65, 3754-3760. (b) For asymmetric Mannich reactions, see: Vicario, J. L.; Badía, D.; Carrillo, L. J. Org. Chem. 2001, 66, 9030-9032; Org. Lett. 2001, 3, 773-776.
33. (a) For use of pseudoephedrine as a chiral auxiliary for asymmetric aldol reaction see: Vicario, J. L.; Badía, D.; Domínguez, E.; Rodríguez, M.; Carrillo, L. J. Org. Chem. 2000, 65, 3754-3760. (b) For asymmetric Mannich reactions, see: Vicario, J. L.; Badía, D.; Carrillo, L. J. Org. Chem. 2001, 66, 9030-9032; Org. Lett. 2001, 3, 773-776.
34. (a) For use of pseudoephedrine as a chiral auxiliary for asymmetric aldol reaction see: Vicario, J. L.; Badía, D.; Domínguez, E.; Rodríguez, M.; Carrillo, L. J. Org. Chem. 2000, 65, 3754-3760. (b) For asymmetric Mannich reactions, see: Vicario, J. L.; Badía, D.; Carrillo, L. J. Org. Chem. 2001, 66, 9030-9032; Org. Lett. 2001, 3, 773-776.
35. The reactions were rapid and did not require the presence of LiCl. For the use of LiCl to accelerate the alkylation reactions of pseudoephedrine amide enolates, see ref 9b.
36. 4), and concentrated in vacuo to afford a yellow oil. Purification by flash chromatography (1:1.5 hexanes/EtOAc) afforded 22a as a colorless oil (5.79 g, 76%).
37. Details are provided as Supporting Information.
38. Kress, M. H.; Yang, C.; Yasuda, N.; Grabowski, E. J. J. Tetrahedron Lett. 1997, 38, 2633-2636.
39. Racemic samples of the lactones were prepared and used for chiral SFC method development. Details are provided as Supporting Information.