Elsevier

Tetrahedron: Asymmetry

Volume 5, Issue 6, June 1994, Pages 1041-1050
Tetrahedron: Asymmetry

Enantiocontrolled synthesis of chiral propane-1,3-diol derivatives possessing fluorinated quaternary stereogenic centers

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Abstract

A general method for the preparation of chiral propane-1,3-diol derivatives possessing fluorinated quaternary stereogenic centers was established as follows. The diastereoselective alkylation of (1R,3R,4S)-8-phenylmenthyl hydrogen fluoromalonate 9, followed by the reduction of the resulting carboxylic acids 10 – 13 in two steps, provided the alcohols 14 – 17. After protection of the hydroxyl group with p-methoxybenzyl group, the phenylmenthyl esters 21 – 24 were converted into chiral propane-1,3-diols 25 and 30 – 32 via the acids 29.

Chiral propane-1,3-diols possessing fluorine atom at the C2 position were synthesized through diastereoselective alkylation of 8-phenylmenthyl hydrogen fluoromalonate.

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