Temperature dependent reversal of stereochemistry in enantioselective conjugate amine additions

Tetrahedron

Volumn 58, Issue 41, 2002, Pages 8357-8363

  Sibi, Mukund P ^a   Gorikunti, Uma ^a   Liu, Mei ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

Achiral template; Chiral Lewis acid; Enantiomers

Indexed keywords

AMINE; BISOXAZOLINE; BROMINE DERIVATIVE; LEWIS ACID; MAGNESIUM BROMIDE; OXAZOLIDINONE DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; DISSOCIATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0037037983     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00988-2     Document Type: Article

References (51)

1. For recent monographs see: (a) Ojima I., Catalytic Asymmetric Synthesis. 2000;Wiley-VCH, New York, (b) Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. 1999;Springer, New York.
2. For recent monographs see: (a) Ojima I., Catalytic Asymmetric Synthesis. 2000;Wiley-VCH, New York, (b) Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. 1999;Springer, New York.
3. For a recent review on reversal of selectivity see: Sibi M.P., Liu M. Curr. Org. Chem. 5:2001;719.
4. For an extensive review on the effect of reaction temperature on selectivity see: Buschmann H., Scharf H.-D., Hoffmann N., Esser P. Angew. Chem., Int. Ed. Engl. 30:1991;477.
5. For examples of reversal of selectivity with temperature see: (a) Inoue Y., Yokoyama T., Yamasaki N., Tai A. Nature. 341:1989;225 (b) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Am. Chem. Soc. 111:1989;6480 (c) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 57:1992;1332 (d) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 58:1993;1011 (e) Pracejus H., Matje H.S. J. Prakt. Chem. 24:1964;195.
6. For examples of reversal of selectivity with temperature see: (a) Inoue Y., Yokoyama T., Yamasaki N., Tai A. Nature. 341:1989;225 (b) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Am. Chem. Soc. 111:1989;6480 (c) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 57:1992;1332 (d) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 58:1993;1011 (e) Pracejus H., Matje H.S. J. Prakt. Chem. 24:1964;195.
7. For examples of reversal of selectivity with temperature see: (a) Inoue Y., Yokoyama T., Yamasaki N., Tai A. Nature. 341:1989;225 (b) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Am. Chem. Soc. 111:1989;6480 (c) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 57:1992;1332 (d) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 58:1993;1011 (e) Pracejus H., Matje H.S. J. Prakt. Chem. 24:1964;195.
8. For examples of reversal of selectivity with temperature see: (a) Inoue Y., Yokoyama T., Yamasaki N., Tai A. Nature. 341:1989;225 (b) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Am. Chem. Soc. 111:1989;6480 (c) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 57:1992;1332 (d) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 58:1993;1011 (e) Pracejus H., Matje H.S. J. Prakt. Chem. 24:1964;195.
9. For examples of reversal of selectivity with temperature see: (a) Inoue Y., Yokoyama T., Yamasaki N., Tai A. Nature. 341:1989;225 (b) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Am. Chem. Soc. 111:1989;6480 (c) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 57:1992;1332 (d) Inoue Y., Yokoyama T., Yamasaki N., Tai A. J. Org. Chem. 58:1993;1011 (e) Pracejus H., Matje H.S. J. Prakt. Chem. 24:1964;195.
10. For a recent review see: Sibi M.P., Manyem S. Tetrahedron. 56:2000;8033.
11. (a) Sibi M.P., Shay J.J., Liu M., Jasperse C.P. J. Am. Chem. Soc. 120:1998;6615.
12. (b) Sibi M.P., Liu M. Enantiomer. 4:1999;575.
13. (c) Sibi M.P., Liu M. Org. Lett. 2:2000;3393.
14. (d) Sibi M.P., Liu M. Org. Lett. 3:2001;4181.
15. For a recent study see: Sibi M.P., Sausker J.B. J. Am. Chem. Soc. 124:2002;983. and references cited therein.
16. For the use of oxazolidinone template in conjugate amine addition see: Falborg L., Jørgensen K.A. J. Chem. Soc., Perkin Trans. 1. 1996;2823.
17. Previous work from our laboratory has shown that 30 mol% of the chiral Lewis acid is generally optimal for obtaining high chemical yield and selectivity. Increasing the catalytic loading to one full equivalent in the present work was analogous to prior results and also led to a decrease in enantioselectivity.
18. (a) 4,4-Disubstituted oxazolidinones have been occasionally employed in enantioselective transformations. For another example of selectivity reversal by changing the template from oxazolidinone to 4,4-dimethyloxazolidinone see: Kanemasa S., Kanai T. J. Am. Chem. Soc. 122:2000;10710. For the use of 4,4-substituted oxazolidinone in radical reactions see: (b) Murakata M., Tsutsui H., Hoshino O. Org. Lett. 3:2001;299 (c) Sibi M.P., Ji J., Wu J.H., Gurtler S., Porter N.A. J. Am. Chem. Soc. 118:1996;9200 (d) Fhal A.-R., Renaud P. Tetrahedron Lett. 38:1997;2661.
19. (a) 4,4-Disubstituted oxazolidinones have been occasionally employed in enantioselective transformations. For another example of selectivity reversal by changing the template from oxazolidinone to 4,4-dimethyloxazolidinone see: Kanemasa S., Kanai T. J. Am. Chem. Soc. 122:2000;10710. For the use of 4,4-substituted oxazolidinone in radical reactions see: (b) Murakata M., Tsutsui H., Hoshino O. Org. Lett. 3:2001;299 (c) Sibi M.P., Ji J., Wu J.H., Gurtler S., Porter N.A. J. Am. Chem. Soc. 118:1996;9200 (d) Fhal A.-R., Renaud P. Tetrahedron Lett. 38:1997;2661.
20. (a) 4,4-Disubstituted oxazolidinones have been occasionally employed in enantioselective transformations. For another example of selectivity reversal by changing the template from oxazolidinone to 4,4-dimethyloxazolidinone see: Kanemasa S., Kanai T. J. Am. Chem. Soc. 122:2000;10710. For the use of 4,4-substituted oxazolidinone in radical reactions see: (b) Murakata M., Tsutsui H., Hoshino O. Org. Lett. 3:2001;299 (c) Sibi M.P., Ji J., Wu J.H., Gurtler S., Porter N.A. J. Am. Chem. Soc. 118:1996;9200 (d) Fhal A.-R., Renaud P. Tetrahedron Lett. 38:1997;2661.
21. (a) 4,4-Disubstituted oxazolidinones have been occasionally employed in enantioselective transformations. For another example of selectivity reversal by changing the template from oxazolidinone to 4,4-dimethyloxazolidinone see: Kanemasa S., Kanai T. J. Am. Chem. Soc. 122:2000;10710. For the use of 4,4-substituted oxazolidinone in radical reactions see: (b) Murakata M., Tsutsui H., Hoshino O. Org. Lett. 3:2001;299 (c) Sibi M.P., Ji J., Wu J.H., Gurtler S., Porter N.A. J. Am. Chem. Soc. 118:1996;9200 (d) Fhal A.-R., Renaud P. Tetrahedron Lett. 38:1997;2661.
22. For a definition of 'inversion temperature' and the effect of temperature on selectivity, see: Cainelli G., Giacomini D., Galletti P. Chem. Commun. 1999;567.
23. The inversion temperature was derived by plotting ee vs. temperature.
24. In a full account on conjugate amine additions to enamides, we have explored the effect of solvents in some detail. Dichloromethane was determined to be optimal in these experiments. See: Sibi, M. P.; Liu, M.; Shay, J. J. J. Org. Chem., submitted for publication.
25. For the synthesis of this template see Ref. 10b.
26. For the synthesis of 4,4-dimethylpyrrollidinone see: (a) Moffett R.B. Organic Syntheses. Coll. Vol. IV:1963;Wiley, New York. p 357 (b) Osby J.O., Ganem B. Tetrahedron Lett. 26:1985;6413.
27. For the synthesis of 4,4-dimethylpyrrollidinone see: (a) Moffett R.B. Organic Syntheses. Coll. Vol. IV:1963;Wiley, New York. p 357 (b) Osby J.O., Ganem B. Tetrahedron Lett. 26:1985;6413.
28. See Section 2 for details.
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30. For a recent example see: Sibi M.P., Rheault T.R. J. Am. Chem. Soc. 122:2000;8873.
31. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
32. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
33. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
34. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
35. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
36. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
37. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
38. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
39. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
40. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
41. For examples of reactions proceeding with higher enantioselectivity at higher temperatures see: (a) Lautens M., Rovis T. J. Am. Chem. Soc. 119:1997;11090 (b) Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163 (c) Stone G.B. Tetrahedron: Asymmetry. 5:1994;465 (d) Dubois L., Fiaud J.-C., Kagan H.B. Tetrahedron: Asymmetry. 6:1995;1097 (e) Burns B., King N.P., Tye H., Studley J.R., Gamble M., Wills M. J. Chem. Soc., Perkins Trans. 1. 1998;1027 (f) Brunel J.M., Maffei M., Buono G. Tetrahedron: Asymmetry. 4:1993;2255 (g) Jones G.B., Heaton S.B., Chapman B.J., Guzel M. Tetrahedron: Asymmetry. 8:1997;3625 (h) Sibi M.P., Cook G.R., Liu P. Tetrahedron Lett. 40:1999;2477 (i) Zhang H., Chan K.S. J. Chem. Soc., Perkin Trans. 1. 1999;381 (j) Muzart J., Henin F., Aboulhoda S.J. Tetrahedron: Asymmetry. 8:1997;381 (k) Wiegers A., Scharf H.-D. Tetrahedron: Asymmetry. 8:1996;2303.
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