Molecular mechanics calculations as predictors of enantioselectivity for chiral nucleophile catalyzed reactions

Tetrahedron

Volumn 58, Issue 41, 2002, Pages 8351-8356

  Taggi, Andrew E ^a   Hafez, Ahmed M ^a   Dudding, Travis ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

lactams; Enantioselective; Ketenes; Molecular mechanics; Monte Carlo conformational searches

Indexed keywords

AMPHOLYTE; BETA LACTAM DERIVATIVE; ESTER DERIVATIVE; KETENE DERIVATIVE;

ACCURACY; ARTICLE; CALCULATION; CATALYST; CHIRALITY; CONFORMATION; CRYSTAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; ENERGY; FORCE; ISOMER; MOLECULAR MECHANICS; MONTE CARLO METHOD; PREDICTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0037037845     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00987-0     Document Type: Article

References (37)

1. (a) Jarvo E.R., Evans C.A., Copeland G.T., Miller S.J. J. Org. Chem. 66:2001;5522-5527.
2. (b) Copeland G.T., Miller S.J. J. Am. Chem. Soc. 123:2001;6496-6502.
3. (c) Korbel G.A., Lalic G., Shair M.D. J. Am. Chem. Soc. 123:2001;361-362.
4. (d) Reetz M.T., Becker M.H., Klein H.-W., Stockigt D. Angew. Chem., Int. Ed. 38:1999;1758-1761.
5. (e) Guo J., Wu J., Siuzdak G., Finn M.G. Angew. Chem., Int. Ed. 38:1999;1755-1758.
6. For general reviews see: (f) Reetz M.T. Angew. Chem., Int. Ed. 40:2001;284-310.
7. (g) Jandeleit B., Schaefer D.J., Powers T.S., Turner H.W., Weinberg W.H. Angew. Chem., Int. Ed. 38:1999;2494-2532.
8. (h) Kuntz K.W., Snapper M.L., Hoveyda A.H. Curr. Opin. Chem. Biol. 3:1999;313-319.
9. (i) Francis M.B., Jamison T.F., Jacobsen E.N. Curr. Opin. Chem. Biol. 2:1998;422-428.
10. For a review of recent β-lactam chemistry see: Palomo C., Aizpurua J.M., Ganboa I., Oiarbide M. Eur. J. Org. Chem. 12:1999;3223-3235.
11. (a) Wilmouth R.C., Kassamally S., Westwood N.J., Sheppard R.J., Claridge T.D.W., Aplin R.T., Wright P.A., Pritchard G.J., Schofield C.J. Biochem. 38:1999;7989-7998.
12. b) Taylor P., Anderson V., Dowden J., Flitsch S.L., Turner N.J., Loughran K., Walkinshaw M.D.J. Biol. Chem. 274:1999;24901-24905.
13. Miller M.J. Tetrahedron. 56:2000;. preface.
14. For an extensive review of the use of cinchona alkaloids as catalysts see: (a) Kacprzak K., Gawronski J. Synthesis. 2001;961-998. For a review on catalysis with organic molecules see: (b) Dalko P.I., Moisan L. Angew. Chem., Int. Ed. 40:2001;3726-3748.
15. For an extensive review of the use of cinchona alkaloids as catalysts see: (a) Kacprzak K., Gawronski J. Synthesis. 2001;961-998. For a review on catalysis with organic molecules see: (b) Dalko P.I., Moisan L. Angew. Chem., Int. Ed. 40:2001;3726-3748.
16. (a) Taggi A.E., Hafez A.M., Wack H., Young B., Ferraris D., Lectka T. J. Am. Chem. Soc. 124:2002;6626-6635.
17. (b) France S., Wack H., Hafez A.M., Taggi A.E., Witsel D., Lectka T. Org. Lett. 4:2002;1603-1605.
18. (c) Taggi A.E., Wack H., Hafez A.M., France S., Lectka T. Org. Lett. 4:2002;627-629.
19. (d) Hafez A.M., Taggi A.E., Dudding T., Lectka T. J. Am. Chem. Soc. 123:2001;10853-10859.
20. (e) Hafez A.M., Taggi A.E., Wack H., Drury W.J. III, Lectka T. Org. Lett. 2:2000;3963-3965.
21. (f) Taggi A.E., Hafez A.M., Wack H., Young B., Drury W.J. III, Lectka T. J. Am. Chem. Soc. 122:2000;7831-7832.
22. Imine 4 was first popularized in work by: Tschaen D.H., Turos E., Weinreb S.M. J. Org. Chem. 49:1984;5058-5064.
23. We have also used N-acyl imino esters to form β-lactams as intermediates in the synthesis of substituted aspartic acids: Dudding T., Hafez A.M., Taggi A.E., Wagerle T.R., Lectka T. Org. Lett. 4:2002;387-390.
24. We have previously used imine 4 for the catalytic asymmetric synthesis of amino acids: Ferraris D., Young B., Cox C., Dudding T., Drury W.J. III, Ryzhkov L., Taggi A.E., Lectka T. J. Am. Chem. Soc. 124:2002;67-77.
25. Macromodel V. 7.0 copyright Columbia University 1986-1998, Schrodinger Inc. 1999. See: Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendricksen T., Still W.C. J. Comput. Chem. 11:1990;440-467.
26. It is possible that acid chloride is deprotonated by BQ or PS (without the initial formation of an acylammonium salt) forming free ketene that can then react with the catalyst to form the zwitterionic intermediate ( Scheme 1 ). IR experiments did not show the formation of free ketene, making this scenario seem unlikely, but not impossible. See Ref. 6a as well as: (a) Brady W.T., Scherubel G.A. J. Org. Chem. 39:1974;3790-3791 (b) Brady W.T., Scherubel G.A. J. Am. Chem. Soc. 95:1973;7447-7449 (c) Walborsky H.M. J. Am. Chem. Soc. 74:1952;4962-4963.
27. It is possible that acid chloride is deprotonated by BQ or PS (without the initial formation of an acylammonium salt) forming free ketene that can then react with the catalyst to form the zwitterionic intermediate ( Scheme 1 ). IR experiments did not show the formation of free ketene, making this scenario seem unlikely, but not impossible. See Ref. 6a as well as: (a) Brady W.T., Scherubel G.A. J. Org. Chem. 39:1974;3790-3791 (b) Brady W.T., Scherubel G.A. J. Am. Chem. Soc. 95:1973;7447-7449 (c) Walborsky H.M. J. Am. Chem. Soc. 74:1952;4962-4963.
28. It is possible that acid chloride is deprotonated by BQ or PS (without the initial formation of an acylammonium salt) forming free ketene that can then react with the catalyst to form the zwitterionic intermediate ( Scheme 1 ). IR experiments did not show the formation of free ketene, making this scenario seem unlikely, but not impossible. See Ref. 6a as well as: (a) Brady W.T., Scherubel G.A. J. Org. Chem. 39:1974;3790-3791 (b) Brady W.T., Scherubel G.A. J. Am. Chem. Soc. 95:1973;7447-7449 (c) Walborsky H.M. J. Am. Chem. Soc. 74:1952;4962-4963.
29. (a) Breit B., Zahn S.K. J. Org. Chem. 66:2001;4870-4877.
30. (b) Breit B. Eur. J. Org. Chem. 1998;1123-1134.
31. Halgren T.A. J. Comput. Chem. 17:1996;490-519.
32. Hydrogen bond contacts have been postulated to play similar roles in other catalytic reactions: (a) Ameer F., Drewes S.E., Freese S., Kaye P.T. Synth. Commun. 18:1988;495-500 (b) Vasbinder M.M., Jarvo E.R., Miller S.J. Angew. Chem., Int. Ed. 40:2001;2824-2827.
33. Hydrogen bond contacts have been postulated to play similar roles in other catalytic reactions: (a) Ameer F., Drewes S.E., Freese S., Kaye P.T. Synth. Commun. 18:1988;495-500 (b) Vasbinder M.M., Jarvo E.R., Miller S.J. Angew. Chem., Int. Ed. 40:2001;2824-2827.
34. Brucine has previously been used as an asymmetric catalyst: (a) Kerr W.J., Kirk G., Middlemiss D. Synlett. 10:1995;1085-1086 (b) Griffiths S.P., Johnston P., Vermeer W.A.H., Wells P.B. J. Chem. Soc., Chem. Commun. 21:1994;2431-2432.
35. Brucine has previously been used as an asymmetric catalyst: (a) Kerr W.J., Kirk G., Middlemiss D. Synlett. 10:1995;1085-1086 (b) Griffiths S.P., Johnston P., Vermeer W.A.H., Wells P.B. J. Chem. Soc., Chem. Commun. 21:1994;2431-2432.
36. Because this catalyst is a derived from quinidine, the stereochemistry of the resultant β-lactam should be the opposite of quinine derivatives.
37. Iwabuchi Y., Nakatani M., Yokoyama N., Hatakeyama S. J. Am. Chem. Soc. 121:1999;10219-10220.