Reversal of Diastereoselectivity in a Masked Acyl Cyanide (MAC) Reaction: Synthesis of Protected erythro-β-Hydroxyaspartate Derivatives.

Org Lett

CP3A Organic Synthesis Group and Services Communs, ICMMO, CNRS , Université Paris-Sud, Université Paris-Saclay, 15 rue Georges Clemenceau , 91405 Orsay cedex , France.

Published: April 2019

Using Garner's aldehyde as a substrate, one-pot MAC hydroxyhomologation reactions proceeded in good yields and with anti selectivity for the first time (dr up to 9:1). The products were used to prepare a panel of protected derivatives of erythro-β-hydroxyaspartic acid and erythro-β-hydroxyasparagine as single enantiomers in a few steps.

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http://dx.doi.org/10.1021/acs.orglett.9b00664DOI Listing

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