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2004
Enantioselective syntheses
O 0031
N-α-Benzyloxyacetyl Derivatives of (S)-4-Benzyl-5,5-dimethyloxazolidin-2-one
for the Asymmetric Synthesis of Differentially Protected α,β-Dihydroxyalde50- 025 hydes.
— It is found that various aldehydes undergo boron-mediated addition to oxazolidinone derivatives of type (III) and (X) with excellent syn selectivity. The resulting
α-benzyloxy products can smoothly be converted into protected α,β-dihydroxyaldehydes without loss of stereochemical integrity. However, cleavage of the auxiliary from
amino adducts (XI) is difficult. In most cases opening of the oxazolidinone ring takes
place predominantly or exclusively. — (DAVIES*, S. G.; HUNTER, I. A.;
NICHOLSON, R. L.; ROBERTS, P. M.; SAVORY, E. D.; SMITH, A. D.;
Tetrahedron 60 (2004) 35, 7553-7577; Chem. Res. Lab., Dep. Chem., Univ. Oxford,
Oxford OX1 3TA, UK; Eng.) — Jannicke
2004
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