Nitroaldol reaction catalyzed by tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP)

Synthetic Communications

Volumn 37, Issue 10, 2007, Pages 1653-1657

  Hirata, N ^a   Hayashi, M ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

nitro alcohol; Base catalyst; Henry reaction; Nitroaldol reaction

Indexed keywords

PHOSPHINE DERIVATIVE; TRIS(2,4,6 TRIMETHOXYPHENYL)PHOSPHINE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 34249330306     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701263833     Document Type: Article

References (15)

1. (a) Henry, L. Compt. Rend. 1895, 120, 1265;
2. (b) Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. (eds); Pergamon: Oxford, 1991; Vol. 2, p. 321;
3. (c) Luzzio, F. A. The Henry reaction: Recent examples. Tetrahedron 2001, 57, 915-945.
4. 3P. J. Chem. Soc., Chem. Commun. 1984, 482-483.
5. Matsukawa, S.; Okano, N.; Imamoto, T. Phosphine catalyzed aldol reaction between ketene silyl acetals and aldehydes: Nucleophilic O-Si and C-Si bond cleavage by phosphine. Tetrahedron Lett. 2000, 41, 103-107.
6. Matsukawa, S.; Obu, K. TTMPP catalyzed one-pot silyl ketene acetal-imine condensation route to β-lactams. Chem. Lett. 2004, 33, 1626-1627.
7. Yoshimoto, K.; Kawabata, H.; Nakamichi, N.; Hayashi, M. Tris(2,4,6-trimethoxyphenyl) phosphine (TTMPP): A novel catalyst for selective deacetylation. Chem. Lett. 2001, 30, 934-935.
8. (a) Kawabata, H.; Hayashi, M. Lewis base-catalyzed transformation of α,β-unsaturated aldehydes to saturated carboxylic acids, esters and amides. Tetrahedron Lett. 2002, 43, 5645-5647;
9. (b) Hayashi, M.; Kawabata, H.; Yoshimoto, K.; Tanaka, T. Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Base catalyst in transformation of α,β-unsaturated aldehydes to saturated carboxylic acid derivatives. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 433-445.
10. For other reports using TTMPP reactions, see (a) as a ligand of Pd, Maddock, S. M.; Finn, M. G. Palladium-catalyzed head to head telomerization of isoprene with amines. Organometallics 2000, 19, 2684-2689;
11. N1-likereactions of bicyclic α-amino ethers with sulfur, nitrogen, and carbon nucleophiles: Synthesis of 1-azabicyclo[3,2,2]nonanes functionalized at carbon C2 and C6 with complete stereocontrol. Org. Lett. 2002, 4, 3179-3182.
12. 3N: An efficient promoter for the nitroaldol (Henry) reaction. J. Org. Chem. 1999, 64, 4298-4303.
13. Bulbule, V. J.; Deshpande, V. H.; Velu, S.; Sudalai, A.; Sivasankar, S.; Sathe, V. T. Heterogeneous Henry reaction of aldehydes: Diastereoselective synthesis of nitroalcohol derivatives over Mg-Al hydrotalcites. Tetrahedron 1999, 55, 9325-9332.
14. Lucet, D.; Sabelle, S.; Kostelitz, O.; Gall, T. L.; Mioskowski, C. Eur. Enantioselective synthesis of a-amino acids and monosubstituted 1,2-diamines by conjugate addition of 4-phenyl-2-oxazolidinone to nitroalkenes. Eur. J. Org. Chem. 1999, 64, 2583-2591.
15. Rosini, G.; Ballini, R.; Sorrenti, P. Synthesis of 2-nitroalkanols on alumina surfaces without solvent: A simple, mild and convenient method. Synthesis 1983, 1014-1015.