Literature DB >> 12027658

Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones.

Jacqueline H Smitrovich1, Geneviève N Boice, Chuanxing Qu, Lisa DiMichele, Todd D Nelson, Mark A Huffman, Jerry Murry, James McNamara, Paul J Reider.   

Abstract

[reaction: see text] The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-delta-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted delta-lactones.

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Year:  2002        PMID: 12027658     DOI: 10.1021/ol0259847

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Disodium Salts of Pseudoephedrine-Derived Myers Enolates: Stereoselectivity and Mechanism of Alkylation.

Authors:  Yuhui Zhou; Ivan Keresztes; Samantha N MacMillan; David B Collum
Journal:  J Am Chem Soc       Date:  2019-10-15       Impact factor: 15.419

2.  Direct enantioselective conjugate addition of carboxylic acids with chiral lithium amides as traceless auxiliaries.

Authors:  Ping Lu; Jeffrey J Jackson; John A Eickhoff; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2015-01-08       Impact factor: 15.419

  2 in total

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