Palladium catalyzed stereoselective cross-couplings and acylations of chiral secondary diorganozincs

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 687-690

  Boudier, Andreas ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Acylation; Alkenylation; Palladium catalysis; Stereoselective cross coupling

Indexed keywords

DIORGANOZINC DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; ZINC;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHIRALITY; METAL BINDING; ORGANIC CHEMISTRY; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033593539     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02581-7     Document Type: Article

References (18)

1. Micouin, L.; Oestreich, M.; Knochel, P. Angew. Chem. 1997, 109, 274-276; Int. Ed. Engl. 1997, 36, 245-246.
2. Micouin, L.; Oestreich, M.; Knochel, P. Angew. Chem. 1997, 109, 274-276; Int. Ed. Engl. 1997, 36, 245-246.
3. Darcel, C.; Flachsmann, F.; Knochel, P. J. Chem. Soc. Chem. Commun. 1998, 205-206.
4. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390-2392.
5. Negishi, E.; Liu, F. in Cross Coupling Reactions, Stang, P. J.; Diederich, F., Eds., VCH, Weinheim, 1997, Chapter 1, p. 1-49.
6. Negishi, E.; Takahashi, T.; Baba, S.; van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393-2401.
7. Negishi, E., Bagheri, V.; Chatterjee, S.; Luo, F.-T.; Miller, J. A.; Stoll, A. T. Tetrahedron Lett. 1983, 24, 5181-5184.
8. (a) Brown, H. C.; Mandal, A. K.; Yoon, N. M.; Singaram, B.; Schwier, J. R.; Jadhav, P. K. J. Org. Chem. 1982, 47, 5069-5074.
9. (b) Brown, H. C.; Singaram, B. J. Am. Chem. Soc. 1984, 106, 1797-1800.
10. Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229-8243.
11. (a) Takahashi, Y.; Ito, T.; Sakai, S.; Ishii, Y. J. Chem. Soc. Chem. Commun. 1970, 1065-1066.
12. (b) Rettig, M. F.; Maitlis, P. M. Inorg. Synth. 1990, 9, 3053.
13. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955-958.
14. The relative trans-stereochemistry of products 2 showing the ruring the cross-coupling has been proven in the case of 2b. For this compound, a COSY-NMR experiment showed a NOE correlation between the benzylic methyl group and the neighbouring allylic proton as well as a NOE correlation between the benzylic proton and the vinylic proton.
15. For the palladium catalyzed acylation of cyclic zinc homoenolates, see: (a) Sakami, S.; Houkawa, T.; Asaoka, M.; Takei, H. J. Chem. Soc. Perkin Trans. 1, 1995, 285-6.
16. (b) Houkawa, T.; Ueda, T.; Sakami, S.; Asaoka, M.; Takei, H. Tetrahedron Lett. 1996, 37, 1045-1048.
17. (c) Asaoka, M.; Tanaka, M.; Houkawa, T.; Ueda, T.; Sakami, S.; Takei, H. Tetrahedron 1998, 54, 471-486.
18. 2, hexanes:ether = 49:1) affording 375 mg (58% based on the starting alkene) of pure 8c. The syn:anti ratio (d.r.: 1:99) and enantioselectivity (e.r.: 90.5:9.5) were determined by capillary GC analysis on a chiral cyclodextrin column (CP-Chirasil-Dex CB, Chrompack).