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2005
Pyran derivatives
R 0340
Double Diastereoselective SuperQuat Glycolate Aldol Reactions: Application to
Asymmetric Synthesis of Polyfunctionalized Lactones. — Polyfunctionalized
16- 120 the
lactones are synthesized by double diastereoselective aldol reaction of hydroxyal
dehydes with a chiral glycolate oxazolidinone (R)- or (S)-(I) followed by desilylation
and lactonization. Treatment of product (III) with TBAF in the presence of AcOH
results in formation of the desired lactone (V) as a single diastereoisomer and returning
of the auxiliary. Further treatment with BzCl forms the expected O-benzoyl derivative
(VII), whereas in the case of substrate (VIII) an elimination reaction is observed (to be
continued). — (DAVIES*, S. G.; NICHOLSON, R. L.; SMITH, A. D.; Org. Biomol.
Chem. 2 (2004) 22, 3385-pp; Chem. Res. Lab., Dep. Chem., Univ. Oxford,
Oxford OX1 3TA, UK; Eng.) — S. Adam
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