What is the reason for the difference in Diels-Alder reactivity of isomeric substituted dienes? A case involving 1,3-dienylboronates

Bulletin de la Societe Chimique de France

Volumn 133, Issue 11, 1996, Pages 1143-1148

  Ohanessian, Gilles ^a   Six, Yvan ^a   Lallemand, Jean Yves ^a  

^a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000811861     PISSN: 00378968     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. a) Mikhailov BM, Cherkasova KL, Zh Obshch Khim (1972) 42, 138 and 1744
2. b) Vaultier M, Truchct F, Carboni B, Tetrahedron Lett (1987) 28, 4169
3. Wang X, J Chem Soc, Chem Commun (1991) 1515
4. Renard PY, These de l'université de Paris Sud, Orsay (1993)
5. e) Renard PY, Lallemand JY, Bull Soc Chim Fr (1996) 133, 143
6. f) Six Y, Lallemand JY, unpublished results
7. g) Gamier L, Plunian B, Mortier J, Vaultier M, Tetrahedron Lett (1996) 37, 6699
8. Recent general reviews: a) Pelter A, Smith K, Brown HC, Borane Reagents (Best Synthetic Methods), Academic Press, London, 1988
9. b) Yamamoto Y, Asao N, Chem Rev (1993) 93, 2207, and references therein
10. Brown HC, Ramachandran PV, Pure Appl Chem (1994) 66, 201, and references therein
11. See, for instance: a) Riicker C, Lang D, Sauer J, Friege H, Sustmann R, Chem Der (1980) 113, 1663
12. b) Dauben WG, Baker WR, Tetrahedron Lett (1982) 23, 2011
13. Reeve W, Reichel DM, J Org Chem (1972) 37, 68
14. Roth WR, Lennartz HW, Doering WVE, Dolbier WR Jr, Schmidhauser JC, J Am Chem Soc (1988) 110, 1883
15. Guo H, Karplus M, J Mol Struct (1992) 260, 347
16. Inukai T, Kojima T, J Org Chem (1967) 32, 872
17. Ab initio calculations were run using the HONDO 8.1 program, from MOTECC-90, Dupuis M et al, IBM Corp, Yorktown Heights, NY 12401 (1990); AMI calculations were performed with the MOPAC G.OO program:
18. a) Stewart JJP, QCPE Bull (1983) 3, 101
19. b) Olivella S, ibid (1980) 4, 109
20. s symmetry. Full details about the optimized geometries are available upon request
21. The LUMO coefficient on the boron atom is fairly high, which is consistent with results involving vinylboranes: Singleton A, J Am Chem Soc (1992) 114, 6563