Enantioselective Construction of Sulfur‐Containing Tetrasubstituted Stereocenters via Asymmetric Functionalizations of α‐Sulfanyl Cyclic Ketones

Asymmetric functionalizations of α‐sulfanyl cyclic ketones were realized via chiral phosphoric acid catalyzed enantioselective addition reactions with aldimines, azodicarboxylates and allenamides. A series of chiral organosulfur compounds possessing sulfur‐containing tetrasubstituted stereocenters w...

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Published inAdvanced synthesis & catalysis Vol. 362; no. 16; pp. 3374 - 3379
Main Authors Ye, Xueqian, Pan, Yongkai, Chen, Yunrong, Yang, Xiaoyu
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 19.08.2020
Wiley Subscription Services, Inc
Subjects
allenamides
asymmetric catalysis
Asymmetry
azodicarboxylates
Chemical reactions
Chemistry
Chemistry, Applied
Chemistry, Organic
Enantiomers
Ketones
Mannich-type reaction
organic catalysis
Organosulfur compounds
Phosphoric acid
Physical Sciences
Science & Technology
Sulfur
α-sulfanyl cyclic ketones
BRONSTED ACID
allenamides
ACTIVATION
MICHAEL ADDITION-REACTIONS
azodicarboxylates
OXINDOLES
SULFENYLATION
5H-OXAZOL-4-ONES
asymmetric catalysis
alpha-sulfanyl cyclic ketones
ALCOHOLS
organic catalysis
AMINATION
DIELS-ALDER REACTION
Mannich-type reaction
THIOETHERS
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Summary:Asymmetric functionalizations of α‐sulfanyl cyclic ketones were realized via chiral phosphoric acid catalyzed enantioselective addition reactions with aldimines, azodicarboxylates and allenamides. A series of chiral organosulfur compounds possessing sulfur‐containing tetrasubstituted stereocenters were accessed via these methods, with excellent regioselectivities and high stereoselectivities.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000520