ortho-Diphenylphosphanylbenzoyl-Directed Cuprate Addition to Acyclic Enoates

Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 525-527

  Breit, Bernhard ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Asymmetric synthesis; Copper; Hydroformylations; Synthetic methods

Indexed keywords

EID: 0032473439     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980302)37:4<525::AID-ANIE525>3.0.CO;2-M     Document Type: Article

References (17)

1. a) B. Breit, Angew. Chem. 1996, 108, 3021-3023; Angew. Chem. Int. Ed. Engl. 1996, 35, 2835-2837;
2. a) B. Breit, Angew. Chem. 1996, 108, 3021-3023; Angew. Chem. Int. Ed. Engl. 1996, 35, 2835-2837;
3. b) B. Breit, Liebigs Ann. 1997, 1841-1851;
4. c) B. Breit in Organic Synthesis via Organometallics (Eds.: G. Helmchen, J. Dibo, D. Flubacher, B. Wiese), Vieweg, Braunschweig, 1997, pp. 139-146;
5. d) B. Breit, Chem. Commun. 1997, 591-592.
6. G. R. Pettit, Z. A. Cichacz, F. Gao, M. R. Boyd, J. M. Schmidt, J. Chem. Soc. Chem. Commun. 1994, 1111-1112.
7. a) M. O. Chaney, P. V. Demarco, N. D. Jones, J. L. Occolowitz, J. Am. Chem. Soc. 1974, 96, 1932-1933;
8. b) D. A. Evans, C. E. Sacks, W. A. Kleschick, T. R. Taber, ibid. 1979, 101, 6789-6791.
9. The addition of higher order cuprates to structurally similar acyclic enoates having a methyl-substituted Stereocenter in the δ-position proceeded in a stereorandom fashion: B. H. Lipshutz, Tetrahedron Lett. 1983, 24, 127-130.
10. 3)Li]: J. S. Filippo, Jr., Inorg. Chem. 1978, 17, 275-283.
11. 3)Li]: J. S. Filippo, Jr., Inorg. Chem. 1978, 17, 275-283.
12. The addition of Gilman cuprates to enoates is generally not a synthetically useful reaction. Alternative reaction pathways such as 1,2-addition are often preferred. See ref. [4] and G. H. Posner, Org. React. 1972, 19, 1-113. For more recent reviews on organocuprate chemistry, see B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; N. Krause. A. Gerold. Angew. Chem. 1997, 109, 194-213; Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
13. The addition of Gilman cuprates to enoates is generally not a synthetically useful reaction. Alternative reaction pathways such as 1,2-addition are often preferred. See ref. [4] and G. H. Posner, Org. React. 1972, 19, 1-113. For more recent reviews on organocuprate chemistry, see B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; N. Krause. A. Gerold. Angew. Chem. 1997, 109, 194-213; Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
14. The addition of Gilman cuprates to enoates is generally not a synthetically useful reaction. Alternative reaction pathways such as 1,2-addition are often preferred. See ref. [4] and G. H. Posner, Org. React. 1972, 19, 1-113. For more recent reviews on organocuprate chemistry, see B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; N. Krause. A. Gerold. Angew. Chem. 1997, 109, 194-213; Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
15. The addition of Gilman cuprates to enoates is generally not a synthetically useful reaction. Alternative reaction pathways such as 1,2-addition are often preferred. See ref. [4] and G. H. Posner, Org. React. 1972, 19, 1-113. For more recent reviews on organocuprate chemistry, see B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631; N. Krause. A. Gerold. Angew. Chem. 1997, 109, 194-213; Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
16. 2CuLi was claimed to increase the reactivity and yield of a 1,4-addition: C. Jallabert, H. Riviere, P. W. Tang, J. Organomet. Chem. 1976, 104, 1-8.
17. r = 518.6): C 74.11, H 7.58; found: C 74.08, H 7.63.