Facile synthesis of 2-nitroalkanols mediated with LiAlH4 as catalyst

Synlett

Volumn , Issue 6, 2000, Pages 880-882

  Youn, So Won ^a   Kim, Yong Hae ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

2 nitroalkanol; Henry reaction; LiAlH sub 4 ; Nitroaldol condensation; Nitroalkanes

Indexed keywords

ALDEHYDE; ALKANOL; ALUMINUM DERIVATIVE; ALUMINUM LITHIUM HYDRIDE; FUNGICIDE; LITHIUM DERIVATIVE; NITROALKANE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL BOND; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE;

EID: 0001017497     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. Reviews : a) Rosini, G. In Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 2, p 321.
2. b) Rosini, G.; Ballini, R. Synthesis 1988, 833. and references cited therein.
3. The recent asymmetric Henry reactions : a) Barco, A.; Benetti, S.; Risi, C.; Polloni, G. Tetrahedron Lett. 1996, 37, 7599.
4. b) Sasai, H.; Hiroi, M.; Yamada, Y.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 6031.
5. c) Kieβ, F.-M; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
6. d) McNulty, J.; Mo, R. Chem. Commun. 1998, 933.
7. e) Menzel, A.; Öhrlein, R.; Griesser, H.; Wehner, V.; Jäger, V. Synthesis 1999, 1691.
8. f) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. Engl. 1999, 38, 1931.
9. Mikite, G.; Jakucs, K.; Darvas, F.; Lopata, A. Pestic. Sci. 1982, 13, 557.
10. a) Vaderbilt, B. M.; Hass, H. B. Ind. Eng. Chem. 1940, 32, 34.
11. b) Hass, H. B.; Riley E. F. Chem. Rev. 1943, 32, 373.
12. c) Lichtenthaler, F. W, Angew. Chem., Int. Ed. Engl. 1964, 3, 211,
13. d) Mélot, J.-M.; Texier-Boullet, F.; Foucaud, A. Tetrahedron Lett. 1986, 27, 493.
14. e) Costantino, U.; Curini, M.; Marmottini, F:; Rosati, O.; Pisani, E. Chem. Lett. 1994, 2215.
15. a) Rosini, G.; Ballini, R.; Petrini, M.; Sorrenti, P. Synthesis 1985, 515.
16. b) Bandgar, B. P.; Zirange, M. B.; Wadgaonkar, P. P. Synlett 1996, 149.
17. Rosini, G.; Ballini, R.; Sorrenti, P. Synthesis 1983, 1014.
18. a) Rosini, G.; Ballini, R.; Petrini, M.; Sorrenti, P. Tetrahedron 1984, 40, 3809.
19. b) Ballini, R.; Bosica, G.; Forconi, P. Tetrahedron 1996, 52, 1677.
20. Kiyooka, S.-I.; Tsutsui, T.; Maeda, H.; Kaneko, Y.; Isobe, K. Tetrahedron Lett. 1995, 36, 6531.
21. Ballini, R.; Bosica, G. J. Org. Chem. 1997, 62, 425.
22. Simoni, D.; Invidiata, F. P.; Manfredini, S.; Ferroni, R.; Lampronti, I. Roberti, M.; Pollini, G. P. Tetrahedron Lett. 1997, 38, 2749.
23. Morao, I.; Cossio, F. P. Tetrahedron Lett. 1997, 38, 6461.
24. Kumar, H. M. S.; Reddy, B. V. S.; Yadav, J. S. Chem. Lett. 1998, 637.
25. Bulbule, V. J.; Deshpande, V. H.; Velu, S.; Sudalai, A.; Sivasankar, S.; Sathe, V. T. Tetrahedron 1999, 55, 9325.
26. Kisanga, P. B.; Verkade, J. G. J. Org. Chem. 1999, 64, 4298.
27. a) Seebach, D.; Beck, A. K.; Mukhopdyay, T.; Thomas, E. Helv. Chim. Acta. 1982, 65, 1101.
28. b) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372.
29. 4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give the corresponding 2-nitroalkanol. All the products are known compounds that were fully characterized by spectral data.