Design of Chiral Bifunctional Dialkyl Sulfide Catalysts for Regio‐, Diastereo‐, and Enantioselective Bromolactonization

Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral b...

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Published inChemistry : a European journal Vol. 24; no. 63; pp. 16747 - 16752
Main Authors Nishiyori, Ryuichi, Tsuchihashi, Ayano, Mochizuki, Ayaka, Kaneko, Kazuma, Yamanaka, Masahiro, Shirakawa, Seiji
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 13.11.2018
Wiley Subscription Services, Inc
Subjects
asymmetric synthesis
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Dialkyl sulfides
Enantiomers
lactonizations
organocatalysis
Physical Sciences
Science & Technology
Sulfide
Sulfides
transition states
Urea
Ureas
ORGANIC-SYNTHESIS
SULFUR YLIDES
HYDRANGEAE DULCIS FOLIUM
PHASE-TRANSFER CATALYST
OLEFINIC 1,3-DIOLS
lactonizations
organocatalysis
ALKENES
asymmetric synthesis
transition states
ASYMMETRIC EPOXIDATION
SULFONIUM YLIDES
YLIDE-MEDIATED EPOXIDATION
sulfides
REGIOSELECTIVE BROMOCYCLIZATION
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Abstract Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio‐, diastereo‐, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation. Chiral bifunctional dialkyl sulfide catalysts bearing a urea moiety were designed for enantioselective bromolactonization. The roles of both sulfide and urea moieties on the catalyst are discussed and clarified based on the results of both experimental and theoretical investigation.
AbstractList Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio‐, diastereo‐, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation.
Abstract Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio‐, diastereo‐, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation.
Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under‐developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio‐, diastereo‐, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation. Chiral bifunctional dialkyl sulfide catalysts bearing a urea moiety were designed for enantioselective bromolactonization. The roles of both sulfide and urea moieties on the catalyst are discussed and clarified based on the results of both experimental and theoretical investigation.
Author Tsuchihashi, Ayano
Mochizuki, Ayaka
Kaneko, Kazuma
Shirakawa, Seiji
Nishiyori, Ryuichi
Yamanaka, Masahiro
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  surname: Shirakawa
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  organization: Nagasaki University
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Issue 63
Keywords ORGANIC-SYNTHESIS
SULFUR YLIDES
HYDRANGEAE DULCIS FOLIUM
PHASE-TRANSFER CATALYST
OLEFINIC 1,3-DIOLS
lactonizations
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transition states
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SULFONIUM YLIDES
YLIDE-MEDIATED EPOXIDATION
sulfides
REGIOSELECTIVE BROMOCYCLIZATION
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e_1_2_2_91_2
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Snippet Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain...
Abstract Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts...
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SubjectTerms asymmetric synthesis
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Dialkyl sulfides
Enantiomers
lactonizations
organocatalysis
Physical Sciences
Science & Technology
Sulfide
Sulfides
transition states
Urea
Ureas
Title Design of Chiral Bifunctional Dialkyl Sulfide Catalysts for Regio‐, Diastereo‐, and Enantioselective Bromolactonization
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.201803703
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https://www.ncbi.nlm.nih.gov/pubmed/30203864
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Volume 24
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