Grignard additions to α,β-unsaturated dioxolanones: Preparation of chiral allylic alcohols and protected α-hydroxy aldehydes

B. Heckmann, C. Mioskowski, Rama K. Bhatt, J R Falck

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α,β-Unsaturated dioxolanones derived from mandelic acid smoothly add most Grignard reagents with good to excellent regio- and diastereoselectivities. The adducts are converted to chiral secondary alcohols by peroxidation at low temperature or to protected α-hydroxy aldehydes via ozonolysis.

Original languageEnglish (US)
Pages (from-to)1421-1424
Number of pages4
JournalTetrahedron Letters
Issue number9
Publication statusPublished - Feb 26 1996


ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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