Organocatalytic Enantioselective Functionalization of Cyclic α-Hydroxyamides: Access to Chiral Cyclic Imides and Azapolycyclic Compounds

A highly efficient enantioselective enamine-catalyzed asymmetric conjugate addition has been developed to directly convert unfunctionalized cyclic alpha-hydroxyamides into chiral cyclic alpha-hydroxyamides by reacting with vinyl sulfones, which could be used as versatile azacyclic synthons in the fo...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 46; pp. 8220 - 8224
Main Authors Zhang, Xiao-Qian, Ma, Yuan-Ren, Liu, Yan-Kai
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 24.11.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NITROGEN-CONTAINING HETEROCYCLES
SUCCINIMIDES
ASYMMETRIC-SYNTHESIS
ONE-POT SYNTHESIS
INTERMOLECULAR ADDITION-REACTIONS
ENANTIOMERS
BASE DESYMMETRISATION
STEREOSELECTIVE-SYNTHESIS
DERIVATIVES
ALKALOIDS
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Summary:A highly efficient enantioselective enamine-catalyzed asymmetric conjugate addition has been developed to directly convert unfunctionalized cyclic alpha-hydroxyamides into chiral cyclic alpha-hydroxyamides by reacting with vinyl sulfones, which could be used as versatile azacyclic synthons in the following sequences: (1) as the precursors of cyclic N-acyliminium ions to prepare natural productlike chiral azapolycyclic compounds under acidic conditions and (2) to construct chiral cyclic imides bearing unilateral substituents via oxidation reaction-induced formal desymmetrization.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03182