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2005
Hydroxylamine derivatives
P 0050
Chiral Oxime Ethers in Asymmetric Synthesis. Part 7. O-(1-Phenylbutyl)benzyla Versatile Reagent for the Asymmetric Synthesis of Protected
35- 063 oxyacetaldoxime,
1,2-Aminoalcohols, α-Amino Acid Derivatives, and 2-Hydroxymethyl Nitrogen
Heterocycles Including Iminosugars. — The addition of a range of organolithium
and Grignard reagents to chiral oxime ethers (I) affords the corresponding hydroxylamines (III) in high diastereomeric excess. The only exception is the addition of allylmagnesium bromide (42% d.e.). Compounds (III) are used as intermediates for the synthesis of a wide range of chiral nitrogen-containing compounds like protected 1,2-amino alcohols, α-amino acid derivatives and 2-hydroxymethyl nitrogen heterocycles including iminosugars. — (COOPER, T. S.; LARIGO, A. S.; LAURENT, P.; MOODY*,
C. J.; TAKLE, A. K.; Org. Biomol. Chem. 3 (2005) 7, 1252-1262; Dep. Chem., Univ.
Exeter, Exeter, Devon EX4 4QD, UK; Eng.) — Bartels
2005
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