Rhodium(i)-catalyzed C-S bond formation via enantioselective carbenoid S-H insertion: catalytic asymmetric synthesis of α-thioesters

Asymmetric construction of C-S bonds through transition-metal catalysis is a challenging subject. By using chiral diene as the ligand, we have developed the first rhodium(i)-catalyzed asymmetric carbene insertion approach for C-S bond formation to access sulfur-substituted stereocenters under mild c...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 9; no. 13; pp. 3467 - 3472
Main Authors Sun, Yu-Tuo, Rao, Xiaofeng, Xu, Weici, Xu, Ming-Hua
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.06.2022
Royal Society of Chemistry
Subjects
Asymmetric synthesis
Asymmetry
Bonding
Catalysis
Chemical synthesis
Chemistry
Chemistry, Organic
Enantiomers
Insertion
Organic chemistry
Physical Sciences
Rhodium
Science & Technology
Sulfur
Thioesters
Transition metals
FDA-APPROVED DRUGS
ALKENES
ACTIVATION
METALLO-BETA-LACTAMASE
CYCLOPROPANATION
THIOMANDELIC ACID
SULFUR
INHIBITOR
ACCESS
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Summary:Asymmetric construction of C-S bonds through transition-metal catalysis is a challenging subject. By using chiral diene as the ligand, we have developed the first rhodium(i)-catalyzed asymmetric carbene insertion approach for C-S bond formation to access sulfur-substituted stereocenters under mild conditions, allowing the facile synthesis of a range of potentially valuable alpha-thioesters in high yields with moderate to good enantioselectivities.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 14
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d2qo00164k