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

[Image: see text] 8-Phenylmenthol esters of salicylic acid derivatives undergo efficient Birch reduction and in situ diastereoselective alkylations to afford methoxycyclohexadienes bearing new quaternary stereogenic centers. The use of an ester-based auxiliary is a designed improvement over the use...

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Autores principales: Kozlowski, Ryan A., Nguyen, Hanh T., Lehman, Michael E., Vanderwal, Christopher D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167686/
https://www.ncbi.nlm.nih.gov/pubmed/37040358
http://dx.doi.org/10.1021/acs.joc.3c00306
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author Kozlowski, Ryan A.
Nguyen, Hanh T.
Lehman, Michael E.
Vanderwal, Christopher D.
author_facet Kozlowski, Ryan A.
Nguyen, Hanh T.
Lehman, Michael E.
Vanderwal, Christopher D.
author_sort Kozlowski, Ryan A.
collection PubMed
description [Image: see text] 8-Phenylmenthol esters of salicylic acid derivatives undergo efficient Birch reduction and in situ 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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spelling pubmed-101676862023-05-10 Stereocontrolled Access to Quaternary Centers by Birch Reduction/Alkylation of Chiral Esters of Salicylic Acids Kozlowski, Ryan A. Nguyen, Hanh T. Lehman, Michael E. Vanderwal, Christopher D. J Org Chem [Image: see text] 8-Phenylmenthol esters of salicylic acid derivatives undergo efficient Birch reduction and in situ 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. American Chemical Society 2023-04-11 /pmc/articles/PMC10167686/ /pubmed/37040358 http://dx.doi.org/10.1021/acs.joc.3c00306 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Kozlowski, Ryan A.
Nguyen, Hanh T.
Lehman, Michael E.
Vanderwal, Christopher D.
Stereocontrolled Access to Quaternary Centers by Birch Reduction/Alkylation of Chiral Esters of Salicylic Acids
title Stereocontrolled Access to Quaternary Centers by Birch Reduction/Alkylation of Chiral Esters of Salicylic Acids
title_full Stereocontrolled Access to Quaternary Centers by Birch Reduction/Alkylation of Chiral Esters of Salicylic Acids
title_fullStr Stereocontrolled Access to Quaternary Centers by Birch Reduction/Alkylation of Chiral Esters of Salicylic Acids
title_full_unstemmed Stereocontrolled Access to Quaternary Centers by Birch Reduction/Alkylation of Chiral Esters of Salicylic Acids
title_short Stereocontrolled Access to Quaternary Centers by Birch Reduction/Alkylation of Chiral Esters of Salicylic Acids
title_sort stereocontrolled access to quaternary centers by birch reduction/alkylation of chiral esters of salicylic acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167686/
https://www.ncbi.nlm.nih.gov/pubmed/37040358
http://dx.doi.org/10.1021/acs.joc.3c00306
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