Synfacts 2007(12): 1310-1310  
DOI: 10.1055/s-2007-991334
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Direct Oxyamination Reaction of Aldehydes with Nitrosobenzene

Contributor(s): Benjamin List, Kristina Zumbansen
C. Palomo*, S. Vera, I. Velilla, A. Mielgo, E. Gómez-Bengoa
Universidad del País Vasco, San SebastiÁn, Spain
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22. November 2007 (online)


Palomo and co-workers present an α-oxyamination reaction of aldehydes using α,α-diphenylprolinol trimethylsilyl ether 1 as catalyst. The reaction was carried out with different aldehydes and nitrosobenzene; a subsequent reduction with sodium borohydride provided the corresponding N-hydroxy β-aminoalcohols. Long-chain aldehydes required 16 h at 20 °C to react (up to 75% yield and with er up to 99:1), whereas alkyl and aryl aldehydes only needed 5-30 minutes at 0 °C to room temperature (up to 70% yield and er up to 99:1). Another competing reaction of nitrosobenzene, namely α-aminoxylation of aldehydes, was not observed in any case.