Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines

Journal of Organic Chemistry

Volumn 68, Issue 26, 2003, Pages 9948-9957

  Evans, Jared W ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVITY;

ADDITION REACTIONS; ALCOHOLS; AMINES; AMINO ACIDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

STEREOCHEMISTRY;

2 METHYLPROPANE 2 SULFINIC ACID (2 BENZYLOXYPROPYLIDINE)AMIDE; 2 METHYLPROPANE 2 SULFINIC ACID [2 (TERT BUTYL DIMETHYLSILANYLOXY)PROPYLIDENE]AMIDE; 2 METHYLPROPANE 2 SULFINIC ACID [2 (TERT BUTYL DIPHENYLSILANYLOXY)PROPYLIDENE]AMIDE; ACETIC ACID ESTER; AMINOALCOHOL; BENZYLOXYSULFINYLALDIMINE; BETA AMINOALCOHOL; IMINE; METHYL ACETATE; N TERT BUTANESULFINYLALDIMINE; ORGANOMETALLIC COMPOUND; SILYLOXYSULFINYLALDIMINE; TITANIUM DERIVATIVE; TITANIUM ENOLATE; UNCLASSIFIED DRUG;

ARTICLE; DEPROTECTION REACTION; EPIMERIZATION; GRIGNARD REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; SYNTHESIS;

AMINO ALCOHOLS; IMINES; MAGNESIUM; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; SULFUR COMPOUNDS;

EID: 0345731485     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035224p     Document Type: Article

References (32)

1. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
2. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis, 1st ed.; Springer: Berlin, Germany, 1999.
3. Andersson, M. A.; Epple, R.; Folkin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 472-475. Demko, Z. P.; Bartsch, M.; Sharpless, K. B. Org. Lett. 2000, 2, 2221-2223.
4. Andersson, M. A.; Epple, R.; Folkin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 472-475. Demko, Z. P.; Bartsch, M.; Sharpless, K. B. Org. Lett. 2000, 2, 2221-2223.
5. Hoffman, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045-1056.
6. For a recent review of asymmetric synthesis of vicinal amino alcohols see: Bergmeier, S. C. Tetrahedron 2000, 56, 2561-2576.
7. Reetz, M. Chem. Rev. 1999, 99, 1121-1162.
8. (a) Ishimaru, K.; Tsuru, K.; Yabuta, K.; Wada, M.; Yamamoto, Y.; Akiba, K. Tetrahedron 1996, 52, 13137-13144.
9. (b) Cianelli, G.; Giacomini, D.; Panunzio, M.; Zarantonello, P. Tetrahedron Lett. 1992, 33, 7783.
10. (c) Zietlow, A.; Steckhan, E. J. Org. Chem. 1994, 59, 5658-5661.
11. (a) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051-2054.
12. (b) Tang, T. P.; Volkman S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772-8778.
13. Lui, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278-1284.
14. Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.
15. For additions to α-aminosulfinyl aldimine see: Prakash, G. K. S.; Mandal, M. J. Am. Chem. Soc. 2002, 124, 6538-6539.
16. For an addition to α-alkoxysulfinyl aldimine see: Jung, P. M. J.; Beaudegnies, R.; De Mesmaeker, A.; Wendeborn, S. Tetrahedron Lett. 2003, 44, 293-297.
17. Cram, D. J.; Abd Elhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5828. Stocker, J. H.; Benjamin, B. M.; Collins, C. J. J. Am. Chem. Soc. 1960, 82, 3913.
18. Cram, D. J.; Abd Elhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5828. Stocker, J. H.; Benjamin, B. M.; Collins, C. J. J. Am. Chem. Soc. 1960, 82, 3913.
19. Rutherford, J. L.; Hoffmann, D.; Collum, D. B. J. Am. Chem. Soc. 2002, 124, 264-271.
20. S,2S) silyloxysulfinyl aldimines 1b and 1c in the presence of 2 equiv of TMEDA in THF reversed diastereoselectivities of 5b from 90:10 (Table 2, entry 5) to 11:89 (anti: syn), and in the case of 5c decreased selectivities from 92:8 (Table 2, entry 7) to 69:31.
21. Cianelli, G.; Giacomini, D.; Galletti, P. Eur. J. Org. Chem. 1999, 61-65.
22. Ahn, N. T. Top. Curr. Chem. 1980, 88, 145.
23. Evans, D. Angew. Chem., Int. Ed. 2003, 42, 1761-1765.
24. Addition of EtMgBr to N-tert-butanesulfinyl-a-tert-butyldimethylsilyloxyacetaldimine in the presence of 2 equiv of TMEDA in THF proceeded with 90:10 diastereoselectivity (88:12 diastereoselectivity was reported for the same reaction in toluene).8b
25. Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12-13.
26. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569. Reetz, M. T.; Kesseler, K.; Schmidtberger, S.; Wenderoth, B.; Steinbach, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 989-990.
27. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569. Reetz, M. T.; Kesseler, K.; Schmidtberger, S.; Wenderoth, B.; Steinbach, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 989-990.
28. Tang, T. P.; Ellman, J. A. J. Org. Chem. 2002, 67, 7819-7832.
29. Andres, J. M.; de Elena, N.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1999, 55, 14137-14144.
30. Asao, N.; Shimada, T.; Sudo, T.; Tsukada, N.; Yazawa, K.; Gyoung, Y. S.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1997, 62, 6274-6282.
31. Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317-1320.
32. Gelbcke, M.; Baudet, M.; Hoyois, J.; Van deVliedt, G.; Deleers, M. Nouv. J. Chim. 1983, 7, 41-47.