Steric versus electronic effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines

Tetrahedron Asymmetry

Volumn 10, Issue 19, 1999, Pages 3803-3809

  Chelucci, Giorgio ^a   Deriu, Sebastiane ^a   Pinna, Gerard A ^a   Saba, Antonio ^a   Valenti, Raffaela ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CHALCONE DERIVATIVE; LIGAND; MALONIC ACID DERIVATIVE; NITRILE; OXAZOLINE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033407596     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00368-7     Document Type: Article

References (21)

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2. For reviews, see: Trost, M. B.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. For more recent references on palladium-catalyzed allylic alkylation reactions, see: Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 1604.
3. For reviews, see: Trost, M. B.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. For more recent references on palladium-catalyzed allylic alkylation reactions, see: Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 1604.
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15. The dinitrile 4 is easily accessible from a variety of pyridine derivatives: (a) from 2,6-dibromopyridine by cyanation with CuCN (44%) [Pearse, G. A.; Wisowaty, J. J. Heterocyclic Chem. 1973, 10, 647]; (b) from the N-oxide of 2-pyridinecarbonitrile by cyanation with KCN (84%) [Tani, H. Chem. Pharm. Bull. 1959, 7, 930]; (c) from 2,6- pyridinedicarboxamide by dehydration (52%) [Bancks, R.; Brookes, R. Chem. Ind. (London) 1974, 15, 617]; (d) from 2,6-dimethylpyridine by oxidative ammonolysis (75%) [Glubokovskikh, L. K.; Kan, I. I.; Suvorov, B. V.; Berstenev, S. V. Izv. Akad. Nauk. Kaz. SSR, Ser. Khim. 1985, 3, 90; C. A. 1986, 104, 88395g].
16. The dinitrile 4 is easily accessible from a variety of pyridine derivatives: (a) from 2,6-dibromopyridine by cyanation with CuCN (44%) [Pearse, G. A.; Wisowaty, J. J. Heterocyclic Chem. 1973, 10, 647]; (b) from the N-oxide of 2-pyridinecarbonitrile by cyanation with KCN (84%) [Tani, H. Chem. Pharm. Bull. 1959, 7, 930]; (c) from 2,6-pyridinedicarboxamide by dehydration (52%) [Bancks, R.; Brookes, R. Chem. Ind. (London) 1974, 15, 617]; (d) from 2,6-dimethylpyridine by oxidative ammonolysis (75%) [Glubokovskikh, L. K.; Kan, I. I.; Suvorov, B. V.; Berstenev, S. V. Izv. Akad. Nauk. Kaz. SSR, Ser. Khim. 1985, 3, 90; C. A. 1986, 104, 88395g].
17. The dinitrile 4 is easily accessible from a variety of pyridine derivatives: (a) from 2,6-dibromopyridine by cyanation with CuCN (44%) [Pearse, G. A.; Wisowaty, J. J. Heterocyclic Chem. 1973, 10, 647]; (b) from the N-oxide of 2-pyridinecarbonitrile by cyanation with KCN (84%) [Tani, H. Chem. Pharm. Bull. 1959, 7, 930]; (c) from 2,6- pyridinedicarboxamide by dehydration (52%) [Bancks, R.; Brookes, R. Chem. Ind. (London) 1974, 15, 617]; (d) from 2,6-dimethylpyridine by oxidative ammonolysis (75%) [Glubokovskikh, L. K.; Kan, I. I.; Suvorov, B. V.; Berstenev, S. V. Izv. Akad. Nauk. Kaz. SSR, Ser. Khim. 1985, 3, 90; C. A. 1986, 104, 88395g].
18. The dinitrile 4 is easily accessible from a variety of pyridine derivatives: (a) from 2,6-dibromopyridine by cyanation with CuCN (44%) [Pearse, G. A.; Wisowaty, J. J. Heterocyclic Chem. 1973, 10, 647]; (b) from the N-oxide of 2-pyridinecarbonitrile by cyanation with KCN (84%) [Tani, H. Chem. Pharm. Bull. 1959, 7, 930]; (c) from 2,6- pyridinedicarboxamide by dehydration (52%) [Bancks, R.; Brookes, R. Chem. Ind. (London) 1974, 15, 617]; (d) from 2,6-dimethylpyridine by oxidative ammonolysis (75%) [Glubokovskikh, L. K.; Kan, I. I.; Suvorov, B. V.; Berstenev, S. V. Izv. Akad. Nauk. Kaz. SSR, Ser. Khim. 1985, 3, 90; C. A. 1986, 104, 88395g].
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