Hydrophosphination of α,β-unsaturated esters by primary phosphine-boranes; a useful entry to symmetrical and unsymmetrical phosphine-boranes

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1923-1926

  Bourumeau, Karine ^a   Gaumont, Annie Claude ^a   Denis, Jean Marc ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031575781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00247-5     Document Type: Article

References (8)

1. 1. For a review, see Wolfsberger, W. Chem. Zeit. 1988, 112, 53-68
2. 2. See in particular: King, R.B.; Masler, W.F. J. Am. Chem. Soc., 1977, 99, 4001-4008 and references cited therein.
3. 3. See for exemple Imamoto, T.; Oshiki, T., Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc., 1990, 112 5245-5252
4. 4. Imamoto, T.; Kusumoto, T.; Susuki, N.; Sato, K. J. Am. Chem. Soc., 1985, 107, 5301-5303 and references cited therein.
5. 5. Gourdel, Y.; Pellon, P.; Toupet, L.; Le Corre, M.; Tetrahedron Lett., 1994, 35, 1197-1201
6. 6. Bourumeau, K.; Gaumont, A.C.; Denis, J.M.; J. Organomet. Chem. 1997, in press.
7. 31P NMR. When all the precursor was consumed, the solvent was removed under vacuum and the new product was purified by silica-gel chromatography. Unsymmetrical bis-adduct: An excess of propionaldehyde (3 equivalents) was slowly added under nitrogen to phosphine-borane 2a (7 mmol) in a benzene or a toluene solution (0.4 M). The mixture was stirred at 60°C for 10 h. Then, the solvent was removed under vacuum and compound 7a was purified by silica-gel chromatography. The two diastereomers were not separated.
8. CP = 14.8Hz). 9. Pelter, A.; Smith, K.; Brown H.C.; "Borane reagents", Academic Press, Harcourt Brace Jovanovitch Publishers, London. 1988.