Palladium-catalyzed stereoselective construction of chiral allenes bearing nonadjacent axial and two central chirality

It is challenging to enantioselectively construct molecules bearing multiple nonadjacent stereocenters, in contrast to those bearing a single stereocenter or adjacent stereocenters. Herein, we report an enantio- and diastereoselective synthesis of substituted chiral allenes with nonadjacent axial an...

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Published inOrganic & biomolecular chemistry Vol. 21; no. 42; pp. 8516 - 852
Main Authors Liu, Li-Xia, Huang, Wen-Jun, Yu, Chang-Bin, Zhou, Yong-Gui
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.11.2023
Royal Society of Chemistry
Subjects
Alkylation
Chemistry
Chemistry, Organic
Chirality
Flavonoids
Palladium
Physical Sciences
Science & Technology
Stereoselectivity
ASYMMETRIC-SYNTHESIS
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Abstract It is challenging to enantioselectively construct molecules bearing multiple nonadjacent stereocenters, in contrast to those bearing a single stereocenter or adjacent stereocenters. Herein, we report an enantio- and diastereoselective synthesis of substituted chiral allenes with nonadjacent axial and two central chiral centers through a combination of retro-oxa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation. This methodology exhibits good functional-group compatibility, and the corresponding allenylic alkylated compounds, including flavonoid frameworks, are obtained with good yields and diastereoselectivities and excellent enantioselectivities (all >95% ee). Furthermore, the scalability of the current synthetic protocol was proven by performing a gram-scale reaction. An enantioselective synthesis of substituted chiral allenes with nonadjacent axial and two central chiral centers is reported, using a combination of retro-oxa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation.
AbstractList It is challenging to enantioselectively construct molecules bearing multiple nonadjacent stereocenters, in contrast to those bearing a single stereocenter or adjacent stereocenters. Herein, we report an enantio- and diastereoselective synthesis of substituted chiral allenes with nonadjacent axial and two central chiral centers through a combination of retro-oxa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation. This methodology exhibits good functional-group compatibility, and the corresponding allenylic alkylated compounds, including flavonoid frameworks, are obtained with good yields and diastereoselectivities and excellent enantioselectivities (all >95% ee). Furthermore, the scalability of the current synthetic protocol was proven by performing a gram-scale reaction.
It is challenging to enantioselectively construct molecules bearing multiple nonadjacent stereocenters, in contrast to those bearing a single stereocenter or adjacent stereocenters. Herein, we report an enantio- and diastereoselective synthesis of substituted chiral allenes with nonadjacent axial and two central chiral centers through a combination of retro-oxa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation. This methodology exhibits good functional-group compatibility, and the corresponding allenylic alkylated compounds, including flavonoid frameworks, are obtained with good yields and diastereoselectivities and excellent enantioselectivities (all >95% ee). Furthermore, the scalability of the current synthetic protocol was proven by performing a gram-scale reaction. An enantioselective synthesis of substituted chiral allenes with nonadjacent axial and two central chiral centers is reported, using a combination of retro-oxa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation.
It is challenging to enantioselectively construct molecules bearing multiple nonadjacent stereocenters, in contrast to those bearing a single stereocenter or adjacent stereocenters. Herein, we report an enantio- and diastereoselective synthesis of substituted chiral allenes with nonadjacent axial and two central chiral centers through a combination of retro-oxa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation. This methodology exhibits good functional-group compatibility, and the corresponding allenylic alkylated compounds, including flavonoid frameworks, are obtained with good yields and diastereoselectivities and excellent enantioselectivities (all >95% ee). Furthermore, the scalability of the current synthetic protocol was proven by performing a gram-scale reaction.It is challenging to enantioselectively construct molecules bearing multiple nonadjacent stereocenters, in contrast to those bearing a single stereocenter or adjacent stereocenters. Herein, we report an enantio- and diastereoselective synthesis of substituted chiral allenes with nonadjacent axial and two central chiral centers through a combination of retro-oxa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation. This methodology exhibits good functional-group compatibility, and the corresponding allenylic alkylated compounds, including flavonoid frameworks, are obtained with good yields and diastereoselectivities and excellent enantioselectivities (all >95% ee). Furthermore, the scalability of the current synthetic protocol was proven by performing a gram-scale reaction.
Author Liu, Li-Xia
Huang, Wen-Jun
Zhou, Yong-Gui
Yu, Chang-Bin
AuthorAffiliation Chinese Academy of Sciences
State Key Laboratory of Catalysis
Dalian Institute of Chemical Physics
University of Chinese Academy of Sciences
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Snippet It is challenging to enantioselectively construct molecules bearing multiple nonadjacent stereocenters, in contrast to those bearing a single stereocenter or...
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SubjectTerms Alkylation
Chemistry
Chemistry, Organic
Chirality
Flavonoids
Palladium
Physical Sciences
Science & Technology
Stereoselectivity
Title Palladium-catalyzed stereoselective construction of chiral allenes bearing nonadjacent axial and two central chirality
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