Stereocontrolled Access to Quaternary Centers by Birch Reduction/Alkylation of Chiral Esters of Salicylic Acids.

J Org Chem

Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, United States.

Published: May 2023

8-Phenylmenthol esters of salicylic acid derivatives undergo efficient Birch reduction and diastereoselective alkylations to afford methoxycyclohexadienes bearing new quaternary stereogenic centers. The use of an ester-based auxiliary is a designed improvement over the use of prolinol-derived amides, which are expensive and often very difficult to cleave.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167686PMC
http://dx.doi.org/10.1021/acs.joc.3c00306DOI Listing

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