Tandem Hass-Bender/Henry reaction for the synthesis of dimethylnitro alcohols from benzylic halides

Tetrahedron Letters

Volumn 46, Issue 27, 2005, Pages 4535-4538

  Klein, Thomas A ^a   Schkeryantz, Jeffrey M ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

Hass Bender reaction; Henry reaction; Tandem reaction; TBAF

Indexed keywords

2 NITROPROPANE; ALCOHOL DERIVATIVE; BENZYL DERIVATIVE; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM FLUORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ONE POT SYNTHESIS; OXIDATION;

EID: 20344393862     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.021     Document Type: Article

References (23)

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8. HMPP has previously been used as a base in the Henry reaction; see: D. Simoni, F.P. Invidiata, S. Manfrenidi, R. Ferroni, I. Lampronti, M. Roberti, and G.P. Pollini Tetrahedron Lett. 38 1997 2749
9. 3: C 52.30, H 5.27, N 6.10; Found: C 52.16, H 5.22, N 6.05
10. 2 provided a quantitative conversion to the corresponding aldehyde
11. TBAF was purchased from Aldrich and used as received. No attempt was made to quantify or remove water in the TBAF solution
12. For an example of an in situ generation of the free base of this compound see: S.J. Wittenberger, W.R. Baker, and B.G. Donner Tetrahedron 49 1993 1547 1556
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18. The subsequent Henry reaction was not observed under the conditions reported by Kornblum
19. N1 reaction manifold is located in the following: N. Kornblum Angew. Chem., Int. Ed. Engl. 14 1975 734 744
20. V. Beraud, P. Perfetti, C. Pfister, M. Kaafarani, P. Vanelle, and M.P. Crozet Tetrahedron 54 1998 4923 4934
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22. The importance in the nature of the leaving group has been reported: R.C. Kerber, G.W. Urry, and N. Kornblum J. Am. Chem. Soc. 87 1965 4520
23. N. Kornblum, P. Pink, and K. Yorka J. Am. Chem. Soc. 83 1961 2779