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. 2008 May 5;49(19):3162-3164.
doi: 10.1016/j.tetlet.2008.03.011.

A mild, efficient method for the oxidation of alpha-diazo-beta-hydroxyesters to alpha-diazo-beta-ketoesters

Puhui Li  1 , Max M Majireck, Ilia Korboukh, Steven M Weinreb
Affiliations

A mild, efficient method for the oxidation of alpha-diazo-beta-hydroxyesters to alpha-diazo-beta-ketoesters

Puhui Li et al. Tetrahedron Lett. .

Abstract

A wide variety of alpha-diazo-beta-ketoesters can be prepared in good overall yields via a two-step sequence involving addition of ethyl lithiodiazoacetate to aliphatic, aromatic and conjugated aldehydes followed by mild oxidation with the Dess-Martin periodinane.

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Scheme 1
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References

    1. Regitz M. Angew. Chem. Int. Ed. 1967;6:733. For reviews and lead references see.
    2. Kurti L, Czako B. Strategic Applications of Named Reactions in Organic Synthesis. Elsevier; London: 2005. p. 376.
    1. Moody CJ, Taylor RJ. Tetrahedron Lett. 1987;28:5351. See inter alia.
    2. Padwa A, Kulkarni YS, Zhang Z. J. Org. Chem. 1990;55:4144.
    3. Moody CJ, Morfitt CN. Synthesis. 1998:1039.
    4. Hasegawa K, Arai S, Nishida A. Tetrahedron. 2006;62:1390.
    5. Varala R, Engula R, Nuvula S, Adapa SR. Tetrahedron Lett. 2006;47:877.
    6. Kantam ML, Chakrapani L, Ramani T. Tetrahedron Lett. 2007;48:6121.
    1. Deng G, Xu B, Wang J. Tetrahedron. 2005;61:10811.
    1. Bagley MC, Hind SL, Moody CJ. Tetrahedron Lett. 2000;41:6897.
    2. Davies JR, Kane PD, Moody CJ, Slawin AMZ. J. Org. Chem. 2005;70:5840. - PubMed
    3. Davies JR, Kane PD, Moody CJ. J. Org. Chem. 2005;70:7305. - PubMed
    1. Moody CJ, Taylor RJ. Tetrahedron. 1990;46:6525.
    2. Padwa A, Dean DC, Osterhout MH, Precedo L, Semones MA. J. Org. Chem. 1994;59:5347.

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