Stereoselective synthesis of 5,6-disubstituted-3,4-dihydro-1H-pyridin-2-ones, a new class of non-biaryl atropisomeric compounds. Part 1

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 611-614

  Jabin, Ivan ^a   Monnier Benoit, Nicolas ^a   Le Gac, Stéphane ^a   Netchitaïlo, Pierre ^a  

^a UNIVERSITÉ DU HAVRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; KETONE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; EPIMERIZATION; GAS CHROMATOGRAPHY; HIGH TEMPERATURE; MASS SPECTROMETRY; MICHAEL ADDITION; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; THERMAL ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 0037433965     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02583-2     Document Type: Article

References (39)

1. Eliel E.L., Wilen S.H., Mander L.N. Stereochemistry of Organic Compounds. 1994;1142-1155 John Wiley and Sons, New York.
2. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;Wiley, New York.
3. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951.
4. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
5. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
6. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
7. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
8. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
9. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
10. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
11. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
12. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
13. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
14. For a review see: (a) Clayden, J. Angew. Chem. Int. Ed. Engl. 1997, 9, 949-951. For recent leading references on axially chiral anilides see: (b) Ates, A. Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130-5131; (c) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Tagushi, T. J. Org. Chem. 2000, 65, 1108-1114; (d) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033-7040; (e) Hugues, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607-7610. Axially chiral 1-naphtamides: (f) Dai, W.-M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603-1613; (g) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166; (h) Clayden, J.; Helliwell, M.; McCarty, C.; Westlund, N. J. Chem. Soc. Perkin Trans. 1, 2000, 3232-3249; (i) Thayumanavan, S.; Beak, P.; Curran, D.P. Tetrahedron Lett. 1996, 37, 2899-2902. Axially chiral benzamides: (j) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695-698; (k) Clayden, J.; Pink, J. H.; Samreen, A. Y. Tetrahedron Lett. 1998, 39, 105-108. See also for atropisomeric pyrazinones: (l) Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93-100.
15. See Refs 1a,c. Koide, H.; Uemura, M. Chem. Commun. 1998, 2483.
16. See Refs 1a,e,f,g. (a) Chen, Y.; Smith, M. D.; Shimizu, K. D. Tetrahedron Lett. 2001, 42, 7185-7187; (b) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279-3283.
17. See Refs 1a,e,f,g. (a) Chen, Y.; Smith, M. D.; Shimizu, K. D. Tetrahedron Lett. 2001, 42, 7185-7187; (b) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279-3283.
18. (a) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812; (b) Jabin, I.; Revial, G.; Pfau, M.; Decroix B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904; (c) Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymmetry 2000, 11, 4975-4983; (d) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261; (e) Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827; (f) Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron Asymmetry 2001, 12, 1683-1688; (g) Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymmetry 2002, 13, 563-567. See also: Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493-2500. d'Angelo, J.; Cavé, C.; Desmaële, D. Israel Journal of Chemistry 1997, 37, 81-85.
19. (a) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812; (b) Jabin, I.; Revial, G.; Pfau, M.; Decroix B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904; (c) Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymmetry 2000, 11, 4975-4983; (d) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261; (e) Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827; (f) Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron Asymmetry 2001, 12, 1683-1688; (g) Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymmetry 2002, 13, 563-567. See also: Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493-2500. d'Angelo, J.; Cavé, C.; Desmaële, D. Israel Journal of Chemistry 1997, 37, 81-85.
20. (a) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812; (b) Jabin, I.; Revial, G.; Pfau, M.; Decroix B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904; (c) Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymmetry 2000, 11, 4975-4983; (d) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261; (e) Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827; (f) Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron Asymmetry 2001, 12, 1683-1688; (g) Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymmetry 2002, 13, 563-567. See also: Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493-2500. d'Angelo, J.; Cavé, C.; Desmaële, D. Israel Journal of Chemistry 1997, 37, 81-85.
21. (a) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812; (b) Jabin, I.; Revial, G.; Pfau, M.; Decroix B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904; (c) Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymmetry 2000, 11, 4975-4983; (d) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261; (e) Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827; (f) Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron Asymmetry 2001, 12, 1683-1688; (g) Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymmetry 2002, 13, 563-567. See also: Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493-2500. d'Angelo, J.; Cavé, C.; Desmaële, D. Israel Journal of Chemistry 1997, 37, 81-85.
22. (a) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812; (b) Jabin, I.; Revial, G.; Pfau, M.; Decroix B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904; (c) Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymmetry 2000, 11, 4975-4983; (d) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261; (e) Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827; (f) Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron Asymmetry 2001, 12, 1683-1688; (g) Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymmetry 2002, 13, 563-567. See also: Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493-2500. d'Angelo, J.; Cavé, C.; Desmaële, D. Israel Journal of Chemistry 1997, 37, 81-85.
23. (a) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812; (b) Jabin, I.; Revial, G.; Pfau, M.; Decroix B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904; (c) Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymmetry 2000, 11, 4975-4983; (d) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261; (e) Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827; (f) Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron Asymmetry 2001, 12, 1683-1688; (g) Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymmetry 2002, 13, 563-567. See also: Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493-2500. d'Angelo, J.; Cavé, C.; Desmaële, D. Israel Journal of Chemistry 1997, 37, 81-85.
24. (a) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812; (b) Jabin, I.; Revial, G.; Pfau, M.; Decroix B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904; (c) Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymmetry 2000, 11, 4975-4983; (d) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261; (e) Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827; (f) Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron Asymmetry 2001, 12, 1683-1688; (g) Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymmetry 2002, 13, 563-567. See also: Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493-2500. d'Angelo, J.; Cavé, C.; Desmaële, D. Israel Journal of Chemistry 1997, 37, 81-85.
25. (a) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812; (b) Jabin, I.; Revial, G.; Pfau, M.; Decroix B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904; (c) Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymmetry 2000, 11, 4975-4983; (d) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261; (e) Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827; (f) Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron Asymmetry 2001, 12, 1683-1688; (g) Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymmetry 2002, 13, 563-567. See also: Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493-2500. d'Angelo, J.; Cavé, C.; Desmaële, D. Israel Journal of Chemistry 1997, 37, 81-85.
26. (a) Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812; (b) Jabin, I.; Revial, G.; Pfau, M.; Decroix B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904; (c) Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymmetry 2000, 11, 4975-4983; (d) Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261; (e) Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827; (f) Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron Asymmetry 2001, 12, 1683-1688; (g) Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymmetry 2002, 13, 563-567. See also: Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493-2500. d'Angelo, J.; Cavé, C.; Desmaële, D. Israel Journal of Chemistry 1997, 37, 81-85.
27. 3) δ 8.60, 19.05 (2C), 34.71, 35.47, 52.56, 171.9, 206.2.
28. Reaction conditions: azeotropic removal of water by refluxing in toluene in a Dean-Stark apparatus, catalytic amount of TFA, 48 h.
29. 3) δ 8.88, 12.83, 17.75, 19.66, 27.20, 33.95, 45.49, 52.09, 105.2, 126.9 (2C), 127.7, 129.0 (2C), 140.9, 166.6, 181.9, 194.9.
30. 3) δ 1.04 (t, J=7.0 Hz, 3H), 1.13 (t, J=7.0 Hz, 3H), 1.80 (d, J=7.0 Hz, 3H), 2.79 (q, J=7.0 Hz, 2H), 2.87-2.94 (m, 2H), 5.39 (q, J=7.0 Hz, 1H), 6.55 (d, J=3.1 Hz, 1H), 6.60 (d, J=3.1 Hz, 1H), 6.93-7.37 (m, 5H).
31. Celerier J.P., Haddad M., Jacoby D., Lhommet G. Tetrahedron Lett. 28:1987;6597-6600.
32. Grotjahn D.B., Volhart K.P.C. Synthesis. 1993;579-605.
33. Phenyl acrylate was prepared according to the literature: Ahlbretch, A.; Codding, D. W. J. Am. Chem. Soc. 1953, 75, 984.
34. See Refs 6b,e,g.
35. Reactions conditions: phenyl acrylate (1-2 equiv.), neat, room temperature, 48 h.
36. 1H NMR analyses.
37. +, HRMS).
38. 3) δ 8.23, 22.14 (2C), 31.26, 52.51, 55.50, 174.4, 208.8.
39. 3) δ 8.60, 25.83 (2C), 32.27, 33.34 (2C), 52.68, 66.70, 174.4, 207.1.