Palladium‐Catalyzed Construction of Phthalides Bearing Two Adjacent Stereocenters through Retro‐oxa‐Michael Addition

Comprehensive Summary Optically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium‐catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing...

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Published inChinese journal of chemistry Vol. 42; no. 23; pp. 3006 - 3012
Main Authors Liu, Li‐Xia, Niu, Tong, Bai, Yu‐Qing, Zhou, Yong‐Gui
Format Journal Article
LanguageEnglish
Published Weinheim WILEY‐VCH Verlag GmbH & Co. KGaA 01.12.2024
Wiley
Wiley Subscription Services, Inc
Subjects
Alkylation
Asymmetric allylic alkylation
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Chemoselectivity
Dynamic kinetic resolution
Lactones
Optical activity
Palladium
Palladium catalysis
Physical Sciences
Retro‐oxa‐Michael addition
Science & Technology
Stereochemistry
Stereoselectivity
Asymmetric allylic alkylation
ASYMMETRIC TRANSFER HYDROGENATION
CARBONATES
Chemoselectivity
ALLYLATION
Dynamic kinetic resolution
Stereochemistry
ALKYLATIONS
TERTIARY
Retro-oxa-Michael addition
Lactones
KETONES
DIPHOSPHINE LIGANDS
Palladium catalysis
ALLYLIC SUBSTITUTION
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Abstract Comprehensive Summary Optically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium‐catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo‐, enantio‐ and diastereoselectivity. Furthermore, gram‐scale experiment underwent smoothly and the transformation of product could build a bridged bicyclic skeleton. A novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium‐catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo‐, enantio‐ and diastereoselectivity.
AbstractList Optically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium‐catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo‐, enantio‐ and diastereoselectivity. Furthermore, gram‐scale experiment underwent smoothly and the transformation of product could build a bridged bicyclic skeleton.
Comprehensive SummaryOptically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium‐catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo‐, enantio‐ and diastereoselectivity. Furthermore, gram‐scale experiment underwent smoothly and the transformation of product could build a bridged bicyclic skeleton.
Comprehensive Summary Optically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium‐catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo‐, enantio‐ and diastereoselectivity. Furthermore, gram‐scale experiment underwent smoothly and the transformation of product could build a bridged bicyclic skeleton. A novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium‐catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo‐, enantio‐ and diastereoselectivity.
Optically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium-catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo-, enantio- and diastereoselectivity. Furthermore, gram-scale experiment underwent smoothly and the transformation of product could build a bridged bicyclic skeleton. A novel dynamic kinetic resolution of isobenzofuranone derivatives through palladium-catalyzed asymmetric allylic alkylation has been developed to synthesize phthalide derivatives bearing vicinal quaternary and tertiary stereocenters with high yields, showing excellent chemo-, enantio- and diastereoselectivity. image
Author Bai, Yu‐Qing
Liu, Li‐Xia
Niu, Tong
Zhou, Yong‐Gui
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  fullname: Niu, Tong
  organization: Chinese Academy of Sciences
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  surname: Zhou
  fullname: Zhou, Yong‐Gui
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  organization: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
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Issue 23
Keywords Asymmetric allylic alkylation
ASYMMETRIC TRANSFER HYDROGENATION
CARBONATES
Chemoselectivity
ALLYLATION
Dynamic kinetic resolution
Stereochemistry
ALKYLATIONS
TERTIARY
Retro-oxa-Michael addition
Lactones
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DIPHOSPHINE LIGANDS
Palladium catalysis
ALLYLIC SUBSTITUTION
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Snippet Comprehensive Summary Optically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of...
Optically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of isobenzofuranone derivatives...
Comprehensive SummaryOptically active phthalides are prevalent in many natural and bioactive products. Herein, a novel dynamic kinetic resolution of...
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SubjectTerms Alkylation
Asymmetric allylic alkylation
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Chemoselectivity
Dynamic kinetic resolution
Lactones
Optical activity
Palladium
Palladium catalysis
Physical Sciences
Retro‐oxa‐Michael addition
Science & Technology
Stereochemistry
Stereoselectivity
Title Palladium‐Catalyzed Construction of Phthalides Bearing Two Adjacent Stereocenters through Retro‐oxa‐Michael Addition
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcjoc.202400612
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Volume 42
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