Palladium-catalyzed asymmetric allenylic alkylation: construction of multiple chiral thiochromanone derivatives

The development of a new strategy for the construction of chiral cyclic sulfide-containing multiple stereogenic centers is highly desirable. Herein, by the combination of base-promoted retro-sulfa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation, the streamlined synthesis of...

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Published inChemical science (Cambridge) Vol. 14; no. 2; pp. 5477 - 5482
Main Authors Liu, Li-Xia, Bai, Yu-Qing, Li, Xiang, Yu, Chang-Bin, Zhou, Yong-Gui
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 24.05.2023
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects
Alkylation
Asymmetry
Chemistry
Chemistry, Multidisciplinary
Chirality
Palladium
Physical Sciences
Science & Technology
AMINATION
MICHAEL-ALDOL REACTIONS
ENANTIOSELECTIVE SYNTHESIS
KINETIC RESOLUTION
ALLYLATION
BEARING
ALLENES
CYCLIZATION
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Summary:The development of a new strategy for the construction of chiral cyclic sulfide-containing multiple stereogenic centers is highly desirable. Herein, by the combination of base-promoted retro-sulfa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation, the streamlined synthesis of chiral thiochromanones containing two central chiralities (including a quaternary stereogenic center) and an axial chirality (allene unit) was successfully realized with up to 98% yield, 49.0 : 1 dr and >99% ee. The development of a new strategy for the construction of chiral cyclic sulfide-containing multiple stereogenic centers is highly desirable.
Bibliography:https://doi.org/10.1039/d3sc01060k
3mk
For ESI and crystallographic data in CIF or other electronic format see DOI
Electronic supplementary information (ESI) available: Experimental procedures and spectroscopic data of compounds. CCDC
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2214958
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:2041-6520
2041-6539
DOI:10.1039/d3sc01060k