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Iterative asymmetric synthesis of protected anti-1,3-polyols

✍ Scribed by Dieter Enders; Thomas Hundertmark

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 226 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00645-0

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✦ Synopsis

A new general method for the iterative asymmetric synthesis of anti-l,3-polyol chains has been developed. The 0t,eg-bisalkylation of 2,2-dimethyl-l,3-dioxan-5-one SAMP-hydrazone 1 with benzyloxymethylchloride as the second electrophile leads to virtually diastereo-and enantiopure substituted 2,2-dimethyl-1,3-dioxan-5-ones with good overall yields. Their deoxygenation and conversion into primary iodides affords the electrophile for the further alkylation of 1. In this way the configurations of all new stereogenic centres are controlled by a single auxiliary.

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