Nucleophilic alkenoylation of aldehydes with metalated α- aminonitriles: Regioselective synthesis of α-hydroxyenones

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5301-5305

  Pierre, Fabrice ^a   Enders, Dieter ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

hydroxyenones; aminonitriles; Metalation; Nucleophilic alkenoylation; Umpolung

Indexed keywords

ALDEHYDE; AMINONITRILE DERIVATIVE; ENONE DERIVATIVE; KETONE DERIVATIVE; NITRILE; SILVER NITRATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG HYDROLYSIS; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0033575458     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00953-3     Document Type: Article

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29. For homoenolate additions with metalated β, γ-unsaturated-α-aminonitriles see: (a) Ahlbrecht, H.; Vonderheid, C. Synthesis 1975, 512-515. (b) Chang, C. J.; Fang, J. M.; Liao, L. F. J. Org. Chem. 1993, 58, 1754-1761. (c) Fang, J. M.; Chang, C. J. J. Chem. Soc., Chem. Commun. 1989, 1787-1788. (d) Fang, J. M.; Chang, H. T.; Lin, C. C. J. Chem. Soc., Chem. Commun. 1988, 1385-1386. (e) Lesur, B.; Toye, J.; Chantrenne, M.; Ghosez, L. Tetrahedron Lett. 1979, 20, 2835-2838.
30. For homoenolate additions with metalated β, γ-unsaturated-α-aminonitriles see: (a) Ahlbrecht, H.; Vonderheid, C. Synthesis 1975, 512-515. (b) Chang, C. J.; Fang, J. M.; Liao, L. F. J. Org. Chem. 1993, 58, 1754-1761. (c) Fang, J.M.; Chang, C. J. J. Chem. Soc., Chem. Commun. 1989, 1787-1788. (d) Fang, J. M.; Chang, H. T.; Lin, C. C. J. Chem. Soc., Chem. Commun. 1988, 1385-1386. (e) Lesur, B.; Toye, J.; Chantrenne, M.; Ghosez, L. Tetrahedron Lett. 1979, 20, 2835-2838.
31. For homoenolate additions with metalated β, γ-unsaturated-α-aminonitriles see: (a) Ahlbrecht, H.; Vonderheid, C. Synthesis 1975, 512-515. (b) Chang, C. J.; Fang, J. M.; Liao, L. F. J. Org. Chem. 1993, 58, 1754-1761. (c) Fang, J.M.; Chang, C. J. J. Chem. Soc., Chem. Commun. 1989, 1787-1788. (d) Fang, J. M.; Chang, H. T.; Lin, C. C. J. Chem. Soc., Chem. Commun. 1988, 1385-1386. (e) Lesur, B.; Toye, J.; Chantrenne, M.; Ghosez, L. Tetrahedron Lett. 1979, 20, 2835-2838.
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34. 2O/petroleum ether 1:3) afforded the hydroxyenone 3g (283 mg, overall yield 78%) as a pale yellow oil.
35. 3 (242.27): C, 74.36; H, 5.82; found: C, 74.42; H, 5.97.
36. (a) Enders, D.; Lotter, H.; Maigrot, N.; Mazaleyrat, J. P.; Welvart, Z. Nouv. J. Chim. 1984, 8, 747-750. (b) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659-666. (c) Enders, D.; Mannes, D.; Raabe, G. Synlett 1992, 837-839. (d) Enders, D.; Gerdes, P.; Kipphardt, H. Angew. Chem. 1990, 102, 226-228; Angew. Chem., Int. Ed. Engl. 1990, 29, 179-181. (e) Enders, D.; Kirchhoff, J.; Lausberg, V. Liebigs Ann. 1996, 1361-1366. (f) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem.1998, 63-72.
37. (a) Enders, D.; Lotter, H.; Maigrot, N.; Mazaleyrat, J. P.; Welvart, Z. Nouv. J. Chim. 1984, 8, 747-750. (b) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659-666. (c) Enders, D.; Mannes, D.; Raabe, G. Synlett 1992, 837-839. (d) Enders, D.; Gerdes, P.; Kipphardt, H. Angew. Chem. 1990, 102, 226-228; Angew. Chem., Int. Ed. Engl. 1990, 29, 179-181. (e) Enders, D.; Kirchhoff, J.; Lausberg, V. Liebigs Ann. 1996, 1361-1366. (f) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem.1998, 63-72.
38. (a) Enders, D.; Lotter, H.; Maigrot, N.; Mazaleyrat, J. P.; Welvart, Z. Nouv. J. Chim. 1984, 8, 747-750. (b) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659-666. (c) Enders, D.; Mannes, D.; Raabe, G. Synlett 1992, 837-839. (d) Enders, D.; Gerdes, P.; Kipphardt, H. Angew. Chem. 1990, 102, 226-228; Angew. Chem., Int. Ed. Engl. 1990, 29, 179-181. (e) Enders, D.; Kirchhoff, J.; Lausberg, V. Liebigs Ann. 1996, 1361-1366. (f) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem.1998, 63-72.
39. (a) Enders, D.; Lotter, H.; Maigrot, N.; Mazaleyrat, J. P.; Welvart, Z. Nouv. J. Chim. 1984, 8, 747-750. (b) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659-666. (c) Enders, D.; Mannes, D.; Raabe, G. Synlett 1992, 837-839. (d) Enders, D.; Gerdes, P.; Kipphardt, H. Angew. Chem. 1990, 102, 226-228; Angew. Chem., Int. Ed. Engl. 1990, 29, 179-181. (e) Enders, D.; Kirchhoff, J.; Lausberg, V. Liebigs Ann. 1996, 1361-1366. (f) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem.1998, 63-72.
40. (a) Enders, D.; Lotter, H.; Maigrot, N.; Mazaleyrat, J. P.; Welvart, Z. Nouv. J. Chim. 1984, 8, 747-750. (b) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659-666. (c) Enders, D.; Mannes, D.; Raabe, G. Synlett 1992, 837-839. (d) Enders, D.; Gerdes, P.; Kipphardt, H. Angew. Chem. 1990, 102, 226-228; Angew. Chem., Int. Ed. Engl. 1990, 29, 179-181. (e) Enders, D.; Kirchhoff, J.; Lausberg, V. Liebigs Ann. 1996, 1361-1366. (f) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem.1998, 63-72.
41. (a) Enders, D.; Lotter, H.; Maigrot, N.; Mazaleyrat, J. P.; Welvart, Z. Nouv. J. Chim. 1984, 8, 747-750. (b) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659-666. (c) Enders, D.; Mannes, D.; Raabe, G. Synlett 1992, 837-839. (d) Enders, D.; Gerdes, P.; Kipphardt, H. Angew. Chem. 1990, 102, 226-228; Angew. Chem., Int. Ed. Engl. 1990, 29, 179-181. (e) Enders, D.; Kirchhoff, J.; Lausberg, V. Liebigs Ann. 1996, 1361-1366. (f) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem.1998, 63-72.
42. (a) Enders, D.; Lotter, H.; Maigrot, N.; Mazaleyrat, J. P.; Welvart, Z. Nouv. J. Chim. 1984, 8, 747-750. (b) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659-666. (c) Enders, D.; Mannes, D.; Raabe, G. Synlett 1992, 837-839. (d) Enders, D.; Gerdes, P.; Kipphardt, H. Angew. Chem. 1990, 102, 226-228; Angew. Chem., Int. Ed. Engl. 1990, 29, 179-181. (e) Enders, D.; Kirchhoff, J.; Lausberg, V. Liebigs Ann. 1996, 1361-1366. (f) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem. 1998, 63-72.