A Practical Preparation of α-Alkoxylithium Reagents: Synthesis of Syn or Anti 1,3-Diols

Article abstract of DOI:10.1021/jo00042a005

Phenylthio acetals 3 are easily prepared from β-hydroxy aldehydes and can be reduced to anti alkyllithiums 7 and subsequently equilibrated to syn alkyllithiums 9 with excellent stereoselectivity and in good overall yield.A practical preparation of 3 and a reductive lithiation procedure using catalytic naphthalene makes these alkyllithium reagents conveniently available on a multigram scale.