Unusual reversal of regioselectivity in antibody-mediated aldol additions with unsymmetrical methyl ketones

Tetrahedron

Volumn 60, Issue 3, 2004, Pages 619-632

  Maggiotti, V ^a   Bahmanyar, S ^b   Reiter, M ^a   Resmini, M ^c   Houk, K N ^b   Gouverneur, V ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Aldol additions; Methyl ketones; Regioselectivity

Indexed keywords

1 (4' NITROPHENYL) 1 HYDROXY 3 HEPTANONE; 1 (4' NITROPHENYL) 1 HYDROXY 3 HEXANONE; 1 (4' NITROPHENYL) 1 HYDROXY 5 METHOXY 3 PENTANONE; 1 (4' NITROPHENYL) 1 HYDROXY 5 METHYLSULFANYL 3 PENTANONE; 1 (4' NITROPHENYL) 1,5 DIHYDROXY 3 PENTANONE; 1 CHLORO 4 (TERT BUTYLDIMETHYLSILANYLOXY) 4 (4' NITROPHENYL)BUTAN 2 ONE; 1 FLUORO 4 (TERT BUTYLDIMETHYLSILANYLOXY) 4 (4' NITROPHENYL) 2 BUTANONE; 1 FLUORO 4 HYDROXY 4 (4 NITROPHENYL)BUTAN 2 ONE; 3 [HYDROXY(4' NITROPHENYL)METHYL] 2 HEXANONE; 3 [HYDROXY(4' NITROPHENYL)METHYL] 2 PENTANONE; 4 (4' NITROPHENYL) 1,4 DIHYDROXY 2 BUTANONE; 4 (4' NITROPHENYL) 3 CHLORO 4 HYDROXY 2 BUTANONE; 4 (4' NITROPHENYL) 3 FLUORO 4 HYDROXY 2 BUTANONE; 4 (4' NITROPHENYL) 3,4 DIHYDROXY 2 BUTANONE; 4 (4' NITROPHENYL) 4 HYDROXY 1 METHOXY 2 BUTANONE; 4 (4' NITROPHENYL) 4 HYDROXY 1 METHYLSULFANYL 2 BUTANONE; 4 (4' NITROPHENYL) 4 HYDROXY 3 HYDROXYMETHYL 3 BUTANONE; 4 (4' NITROPHENYL) 4 HYDROXY 3 METHOXY 2 BUTANONE; 4 (4' NITROPHENYL) 4 HYDROXY 3 METHOXYMETHYL 2 BUTANONE; 4 (4' NITROPHENYL) 4 HYDROXY 3 METHYLSULFANYL 2 BUTANONE; 4 (4' NITROPHENYL) 4 HYDROXY 3 METHYLSULFANYL 3 BUTANONE; 4 (TERT BUTYLDIMETHYLSILANYLOXY) 4 (4' NITROPHENYL) 2 BUTANONE; 4 NITROBENZALDEHYDE; 6 (4' ACETAMIDOPHENYL) 3 ETHYL 4 HYDROXY 2 HEXANONE; 8 (4' ACETAMIDOPHENYL) 6 HYDROXY 4 OCTANONE; ACETONE; ALDEHYDE DERIVATIVE; ANTIBODY; ENAMINE; FRUCTOSE BISPHOSPHATE ALDOLASE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; PRIORITY JOURNAL; THERMODYNAMICS;

EID: 0346964418     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.115     Document Type: Article

References (62)

1. For general reviews on the catalytic enantioselective aldol reaction: (a) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. 3:1999;Springer, Heidelberg. Chapter 29-1 (b) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389 (c) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141 (d) Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. Engl. 39:2000;1352-1375.
2. For general reviews on the catalytic enantioselective aldol reaction: (a) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. 3:1999;Springer, Heidelberg. Chapter 29-1 (b) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389 (c) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141 (d) Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. Engl. 39:2000;1352-1375.
3. For general reviews on the catalytic enantioselective aldol reaction: (a) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. 3:1999;Springer, Heidelberg. Chapter 29-1 (b) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389 (c) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141 (d) Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. Engl. 39:2000;1352-1375.
4. For general reviews on the catalytic enantioselective aldol reaction: (a) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. 3:1999;Springer, Heidelberg. Chapter 29-1 (b) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389 (c) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141 (d) Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. Engl. 39:2000;1352-1375.
5. (a) Mukaiyama T. Org. React. 28:1982;203-331
6. (b) Heathcock C.H. Morrison J.D. Asymmet. Synth. Vol. 3:1984;Academic, New York. Chapter 2
7. (c) Evans D.A., Nelson J.V., Taber T.R. Topics Stereochem. 13:1982;1-115
8. (d) Masamune S., Choy W., Petersen J.S., Sita L.R. Angew. Chem., Int. Engl. 97:1985;1-31
9. (e) Evans D.A., Bartoli J., Shih T.L. J. Am. Chem. Soc. 103:1981;2127-2129.
10. See for example: (a) Keck G.E., Krishnamurthy D. J. Am. Chem. Soc. 117:1995;2363-2365 (b) Mikami K., Matsukawa S., Nagashima M., Funabashi H., Morishima H. Tetrahedron Lett. 38:1997;579-582 (c) Singer R.A., Carreira E.M. Tetrahedron Lett. 38:1997;927-930 (d) Carreira E.M., Singer R.A., Lee W. J. Am. Chem. Soc. 116:1994;8837-8838 (e) Mikami K., Matsukawa S. J. Am. Chem. Soc. 116:1994;4077-4078 (f) Kim Y., Singer R.A., Carreira E.M. Angew. Chem., Int. Ed. 37:1998;1261-1263 (g) Evans D.A., Murry J.A., Kozlowski M.C., Burgey C.S., MacMillan D.W.C. J. Am. Chem. Soc. 119:1997;7893-7894 (h) Kobayashi S., Nagayama S., Busujima T. Chem. Lett. 1999;71-72.
11. See for example: (a) Keck G.E., Krishnamurthy D. J. Am. Chem. Soc. 117:1995;2363-2365 (b) Mikami K., Matsukawa S., Nagashima M., Funabashi H., Morishima H. Tetrahedron Lett. 38:1997;579-582 (c) Singer R.A., Carreira E.M. Tetrahedron Lett. 38:1997;927-930 (d) Carreira E.M., Singer R.A., Lee W. J. Am. Chem. Soc. 116:1994;8837-8838 (e) Mikami K., Matsukawa S. J. Am. Chem. Soc. 116:1994;4077-4078 (f) Kim Y., Singer R.A., Carreira E.M. Angew. Chem., Int. Ed. 37:1998;1261-1263 (g) Evans D.A., Murry J.A., Kozlowski M.C., Burgey C.S., MacMillan D.W.C. J. Am. Chem. Soc. 119:1997;7893-7894 (h) Kobayashi S., Nagayama S., Busujima T. Chem. Lett. 1999;71-72.
12. See for example: (a) Keck G.E., Krishnamurthy D. J. Am. Chem. Soc. 117:1995;2363-2365 (b) Mikami K., Matsukawa S., Nagashima M., Funabashi H., Morishima H. Tetrahedron Lett. 38:1997;579-582 (c) Singer R.A., Carreira E.M. Tetrahedron Lett. 38:1997;927-930 (d) Carreira E.M., Singer R.A., Lee W. J. Am. Chem. Soc. 116:1994;8837-8838 (e) Mikami K., Matsukawa S. J. Am. Chem. Soc. 116:1994;4077-4078 (f) Kim Y., Singer R.A., Carreira E.M. Angew. Chem., Int. Ed. 37:1998;1261-1263 (g) Evans D.A., Murry J.A., Kozlowski M.C., Burgey C.S., MacMillan D.W.C. J. Am. Chem. Soc. 119:1997;7893-7894 (h) Kobayashi S., Nagayama S., Busujima T. Chem. Lett. 1999;71-72.
13. See for example: (a) Keck G.E., Krishnamurthy D. J. Am. Chem. Soc. 117:1995;2363-2365 (b) Mikami K., Matsukawa S., Nagashima M., Funabashi H., Morishima H. Tetrahedron Lett. 38:1997;579-582 (c) Singer R.A., Carreira E.M. Tetrahedron Lett. 38:1997;927-930 (d) Carreira E.M., Singer R.A., Lee W. J. Am. Chem. Soc. 116:1994;8837-8838 (e) Mikami K., Matsukawa S. J. Am. Chem. Soc. 116:1994;4077-4078 (f) Kim Y., Singer R.A., Carreira E.M. Angew. Chem., Int. Ed. 37:1998;1261-1263 (g) Evans D.A., Murry J.A., Kozlowski M.C., Burgey C.S., MacMillan D.W.C. J. Am. Chem. Soc. 119:1997;7893-7894 (h) Kobayashi S., Nagayama S., Busujima T. Chem. Lett. 1999;71-72.
14. See for example: (a) Keck G.E., Krishnamurthy D. J. Am. Chem. Soc. 117:1995;2363-2365 (b) Mikami K., Matsukawa S., Nagashima M., Funabashi H., Morishima H. Tetrahedron Lett. 38:1997;579-582 (c) Singer R.A., Carreira E.M. Tetrahedron Lett. 38:1997;927-930 (d) Carreira E.M., Singer R.A., Lee W. J. Am. Chem. Soc. 116:1994;8837-8838 (e) Mikami K., Matsukawa S. J. Am. Chem. Soc. 116:1994;4077-4078 (f) Kim Y., Singer R.A., Carreira E.M. Angew. Chem., Int. Ed. 37:1998;1261-1263 (g) Evans D.A., Murry J.A., Kozlowski M.C., Burgey C.S., MacMillan D.W.C. J. Am. Chem. Soc. 119:1997;7893-7894 (h) Kobayashi S., Nagayama S., Busujima T. Chem. Lett. 1999;71-72.
15. See for example: (a) Keck G.E., Krishnamurthy D. J. Am. Chem. Soc. 117:1995;2363-2365 (b) Mikami K., Matsukawa S., Nagashima M., Funabashi H., Morishima H. Tetrahedron Lett. 38:1997;579-582 (c) Singer R.A., Carreira E.M. Tetrahedron Lett. 38:1997;927-930 (d) Carreira E.M., Singer R.A., Lee W. J. Am. Chem. Soc. 116:1994;8837-8838 (e) Mikami K., Matsukawa S. J. Am. Chem. Soc. 116:1994;4077-4078 (f) Kim Y., Singer R.A., Carreira E.M. Angew. Chem., Int. Ed. 37:1998;1261-1263 (g) Evans D.A., Murry J.A., Kozlowski M.C., Burgey C.S., MacMillan D.W.C. J. Am. Chem. Soc. 119:1997;7893-7894 (h) Kobayashi S., Nagayama S., Busujima T. Chem. Lett. 1999;71-72.
16. See for example: (a) Keck G.E., Krishnamurthy D. J. Am. Chem. Soc. 117:1995;2363-2365 (b) Mikami K., Matsukawa S., Nagashima M., Funabashi H., Morishima H. Tetrahedron Lett. 38:1997;579-582 (c) Singer R.A., Carreira E.M. Tetrahedron Lett. 38:1997;927-930 (d) Carreira E.M., Singer R.A., Lee W. J. Am. Chem. Soc. 116:1994;8837-8838 (e) Mikami K., Matsukawa S. J. Am. Chem. Soc. 116:1994;4077-4078 (f) Kim Y., Singer R.A., Carreira E.M. Angew. Chem., Int. Ed. 37:1998;1261-1263 (g) Evans D.A., Murry J.A., Kozlowski M.C., Burgey C.S., MacMillan D.W.C. J. Am. Chem. Soc. 119:1997;7893-7894 (h) Kobayashi S., Nagayama S., Busujima T. Chem. Lett. 1999;71-72.
17. See for example: (a) Keck G.E., Krishnamurthy D. J. Am. Chem. Soc. 117:1995;2363-2365 (b) Mikami K., Matsukawa S., Nagashima M., Funabashi H., Morishima H. Tetrahedron Lett. 38:1997;579-582 (c) Singer R.A., Carreira E.M. Tetrahedron Lett. 38:1997;927-930 (d) Carreira E.M., Singer R.A., Lee W. J. Am. Chem. Soc. 116:1994;8837-8838 (e) Mikami K., Matsukawa S. J. Am. Chem. Soc. 116:1994;4077-4078 (f) Kim Y., Singer R.A., Carreira E.M. Angew. Chem., Int. Ed. 37:1998;1261-1263 (g) Evans D.A., Murry J.A., Kozlowski M.C., Burgey C.S., MacMillan D.W.C. J. Am. Chem. Soc. 119:1997;7893-7894 (h) Kobayashi S., Nagayama S., Busujima T. Chem. Lett. 1999;71-72.
18. (a) Yamada Y.M.A., Yoshikawa N., Sasai H., Shibasaki M. Angew. Chem., Int. Ed. Engl. 36:1997;1871-1873
19. (b) Arai T., Yamada Y.M.A., Yamamoto H., Sasai H., Shibasaki M. Chem. Eur. J. 2:1996;1368-1372
20. (c) Yoshikawa N., Yamada Y.M.A., Das J., Sasai H., Shibasaki M. J. Am. Chem. Soc. 121:1999;4168-4178
21. (d) Yamada Y.M.A., Shibasaki M. Tetrahedron Lett. 39:1988;5561-5564
22. (e) Kumagai N., Matsunaga S., Yoshikawa N., Ohshima T., Shibasaki M. Org. Lett. 3:2001;1539-1542.
23. (a) List B., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 122:2000;2395-2396
24. (b) Notz W., List B. J. Am. Chem. Soc. 122:2000;7386-7387
25. (c) List B. Synlett. 11:2001;1675-1686
26. (d) List B., Pojarliev P., Castello C. Org. Lett. 3:2001;573-575
27. (e) List B. Tetrahedron. 58:2002;5573-5590
28. (f) Hoang L., Bahmanyar S., List B. J. Am. Chem. Soc. 125:2003;16-17
29. (g) Bahmanyar S., Houk K.N., Martin H.J., List B. J. Am. Chem. Soc. 125:2003;2475-2479.
30. (a) Trost B.M., Ito H. J. Am. Chem. Soc. 122:2004;12003-12004
31. (b) Trost B.M., Silcoff E.R., Ito H. Org. Lett. 3:2001;2497-2500
32. (c) Trost B.M., Ito H., Silcoff E.R. J. Am. Chem. Soc. 123:2001;3367-3368.
33. (a) Wong C.-H., Whitesides G.M. Enzymes in Synthetic Organic Chemistry. 1994;Pergamon, Oxford
34. (b) Drauz K., Waldmann H. Enzyme Catalysis in Organic Synthesis. 1995;VCH, Weinheim
35. (c) Gijsen H.J.M., Qiao L., Fitz W., Wong C.-H. Chem. Rev. 96:1996;443-476.
36. (a) Wagner J., Lerner R.A., Barbas C.F. III. Science. 270:1995;1797-1800
37. (b) Björnestedt R., Zhong G., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 118:1996;11720-11724
38. (c) Zhong G., Hoffmann T., Lerner R.A., Danishefsky S., Barbas C.F. III. J. Am. Chem. Soc. 119:1997;8131-8132
39. (d) Hoffmann T., Zhong G., List B., Shabat D., Anderson J., Gramatikova S., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 120:1998;2768-2779
40. (e) Zhong G., Shabat D., List B., Anderson J., Sinha S.C., Lerner R.A., Barbas C.F. III. Angew. Chem., Int. Ed. 37:1998;2481-2484
41. (f) List B., Shabat D., Zhong G., Turner J.M., Li A., Bui T., Anderson J., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 121:1999;7283-7291
42. (g) Zhong G., Lerner R.A., Barbas C.F. III. Angew. Chem., Int. Ed. 38:1999;3738-3741.
43. Maggiotti V., Resmini M., Gouverneur V. Angew. Chem., Int. Ed. 41:2002;1012-1014.
44. (a) Hoffmann T., Zhong G., List B., Shabat D., Anderson J., Gramatikova S., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 120:1998;2768
45. (b) Lerner R.A., Barbas C.F. III. Acta Chem. Scand. 36:1996;672-678.
46. (a) Guth J.J., Gross R.L., Carson F.W. J. Org. Chem. 47:1982;2666-2669
47. (b) Guthrie J.P., Cossar J. Can. J. Chem. 64:1986;1250-1266.
48. (a) Adolph H.G., Kamlet M.J. J. Am. Chem. Soc. 88:1966;4761-4763
49. (b) Hine J., Mahone L.G., Liotta C.L. J. Am. Chem. Soc. 89:1967;5911-5920
50. (c) Hine J., Hampton G.K., Menon B.C. J. Am. Chem. Soc. 89:1967;2664-2668
51. (d) Hine J., Sinha A. J. Org. Chem. 49:1984;2186-2190.
52. (a) List B., Shabat D., Barbas C.F. III, Lerner R.A. Chem. Eur. J. 4:1998;881-885
53. (b) Shabat D., List B., Lerner R.A., Barbas C.F. III. Tetrahedron Lett. 40:1999;1437-1440.
54. Maggiotti V., Wong J.-B., Razet R., Cowley A.R., Gouverneur V. Tetrahedron: Asymmetry. 13:2002;1789-1798.
55. Lin J.-F., Wu C.-C., Lien M.-H. J. Phys. Chem. 99:1995;16903-16908.
56. (a) Becke A.D. J. Chem. Phys. 98:1993;1372-1377. see also 5648-5652
57. (b) Lee C., Yang W., Parr R.G. Phys. Rev. B. 37:1988;785-789.
58. (a) Ditchfield R., Hehre W.J., Pople J.A. J. Chem. Phys. 54:1971;724-728
59. (b) Hehre W.J., Ditchfield R., Pople J.A. J. Chem. Phys. 56:1972;2257-2261
60. (c) Hariharan P.C., Pople J.A. Theor. Chim. Acta. 28:1973;213-222.
61. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.R.; Gomperts, R.; Martin, L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.;Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M. P.; Gill, M.W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.;Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98 (Revision A.11); Gaussian, Inc.: Pittsburgh, PA, 1998.
62. Reported energies include zero point energy corrections and were scaled by 0.9806 Scott A.P., Radom L. J. Phys. Chem. 100:1996;16502-16513.