General Method for the Synthesis of Chiral 2,3-Bisarylmethoxy-1,4-Butanediols from l-(+)-Tartrate

Abstract

Various (2S,3S)-2,3-bisarylmethoxy-1,4-butanediols 3a-h were synthesized from l-(+)-tartrate through bisallylether 12. Protection of the primary alcohol as an allyl ether was essential for selective deprotection in the presence of reactive arylmethyl ethers.

Key words

tartaric acid - allyl ether - catalyst - palladium - deprotection

References

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• 4b

  Unpublished result

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8

We assume hydroboration would proceed exclusively because no olefinic signals were observed in the ¹H NMR spectra of crude products.