Journal of Organic Chemistry 2011-06-03

DIBAL-mediated reductive transformation of trans-dimethyl tartrate acetonide into ε-hydroxy α,β-unsaturated ester and its derivatives.

Takashi Tomioka, Yuki Yabe, Tohru Takahashi, Tracy K Simmons

Index: J. Org. Chem. 76(11) , 4669-74, (2011)

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Abstract

Stepwise, selective DIBAL reduction of the acetonide diester derived from tartaric acid followed by the Horner-Emmons reaction effectively provided desymmetrized hydroxy mono-olefination products in a one-pot operation.

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