Reformatsky-type co-mediated synthesis of β-hydroxyphosphonates

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1425-1428

  Orsini, Fulvia ^a  

^a Dipto di Chim Organ e Industriale   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; COBALT COMPLEX; KETONE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0032510301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10819-X     Document Type: Article

References (16)

1. 1. Orsini, F.; Pelizzoni, F.; Pulici, M.; Vallarino, L. M. J. Org. Chem. 1994, 59, 1-4.
2. 2. Orsini, F.; Pulici, M.; Vallarino, L. M. J. Organom. Chem, 1995, 495, 1-5.
3. 3. Orsini, F.; Pulici, M. "Highlights on Recent Advancements in Reformatsky-type Reactions: the Cobalt Approach. In Trends in Organometallic Chemistry: J. Menon Ed., Research Trends Pub., Trivandrum, India, 1994, 1, 625-667.
4. 4. Orsini, F. J. Org. Chem. 1997, 62, 1159-1163.
5. 5. (a) Klein, H. F. Angew. Chemie 1971, 83, 363.
6. (b) Klein, H. F.; Karsch, H. H. Chem. Ber. 1975, 108, 944-955.
7. 6. In the cobalt-mediated Reformatsky-type reaction of α-haloesters with carbonyl compounds the best results were obtained with a 1:1:1 molar ratio of haloester:carbonyl compound:Co(0)-complex.
8. 7. To investigate whether an organomagnesium compound might be involved, a parallel experiment was performed adding the diethyl iodomethylphosphonate and benzaldehyde to magnesium alone in tetrahydrofuran. The amount of diethyl iodomethylphosphonate, benzaldehyde and magnesium were the same in both experiments and so were the other experimental conditions (temperature, time of reaction, speed of stirring). In the absence of cobalt a significant amount of starting material was recovered unchanged: the chief reaction product was dihydrobenzoin, accompanied by a smaller amount of β-hydroxyphosphonate.
9. 8. (a) Imamoto, T.; Sato, K.; Johnson, C. R. Tetrahedron Lett. 1985, 26, 783-786 .
10. (b) Teulade, M. P.; Savignac, P.; Aboujaoude, E. E.; Collignon, N. J. Organom. Chem. 1985, 287, 145-156.
11. (c) Aboujaoude, E. E., Lietjie, S.; Collignon, N.; Teulade, M. P.; Savignac, P. Tetrahedron Lett. 1985, 26, 4435-4438.
12. 9. Mikolajczyk, M.; Balcezewski, P. Synthesis 1984, 691-694.
13. 10. (a) Li, Z.; Racha, S.; Dan, L.; El Subbagh, H.; Abushanab, E. J. Org. Chem. 1993, 58, 5779-5783.
14. (b) Li, Z.; Racha, S.; El-Subbagh, H.; Abushanab, E. Tetrahedron Lett. 1992, 33, 5491-5494.
15. 11. Collard, J. N.; Benezra, C. Tetrahedron Lett. 1982, 23, 3725-3728.
16. 12. Classical "one-pot" Reformatsky reaction of diethyl iodomethylphosphonate with benzaldehyde in dry tetrahydrofuran in the presence of activated zinc turnings failed to give the β-hydroxy phosphonate.