Regio‐ and Enantioselective Synthesis of Sulfone‐Bearing Quaternary Carbon Stereocenters by Pd‐Catalyzed Allylic Substitution

Chiral sulfones are of great importance in medicinal chemistry and chemical synthesis. Efficient methods for preparing enantiomerically enriched sulfone‐containing molecules can therefore be of significant value; such methods, however, are uncommon. Herein, we report the first general palladium‐cata...

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Vydané v:	Angewandte Chemie International Edition Ročník 59; číslo 3; s. 1340 - 1345
Hlavní autori:	Khan, Ajmal, Zhao, Heng, Zhang, Meina, Khan, Shahid, Zhao, Depeng
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	WEINHEIM Wiley 13.01.2020 Wiley Subscription Services, Inc
Vydanie:	International ed. in English
Predmet:	Aliphatic compounds allylic substitution Aromatic compounds asymmetric catalysis Carbon Carbonates Chemical synthesis Chemistry Chemistry, Multidisciplinary cyclic carbonates Enantiomers Organic chemistry Palladium Physical Sciences Science & Technology Sodium Substitution reactions Substrates Sulfones tertiary sulfones ASYMMETRIC-SYNTHESIS DECARBOXYLATIVE CYCLOADDITION ALKYLATION SULFUR asymmetric catalysis CENTERS cyclic carbonates CHIRAL SULFONES S BOND FORMATION VINYLETHYLENE CARBONATES AMINES tertiary sulfones CONSTRUCTION palladium allylic substitution
ISSN:	1433-7851, 1521-3773, 1521-3773
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Abstract	Chiral sulfones are of great importance in medicinal chemistry and chemical synthesis. Efficient methods for preparing enantiomerically enriched sulfone‐containing molecules can therefore be of significant value; such methods, however, are uncommon. Herein, we report the first general palladium‐catalyzed sulfonylation of vinyl cyclic carbonates with sodium sulfinates. A series of enantiomerically enriched tertiary allylic sulfones were synthesized in good yields with excellent enantiomeric ratios. Both aliphatic‐ and aryl‐substituted vinyl cyclic carbonates are suitable reactants with excellent results. This reaction features broad substrates scope, readily available starting materials, excellent regio‐ and enantioselectivity, and synthesis of sulfone‐bearing quaternary carbon stereocenters. Through the sulfonylation of geranyl derived cyclic carbonate 1 h, we achieve the formal total synthesis of (+)‐agelasidine A. The first general example of regio‐ and enantioselective palladium catalyzed allylic sulfonylation of vinyl cyclic carbonates provides an efficient and direct way to construct sulfone‐bearing quaternary carbon stereocenters. A three steps formal total synthesis of (+)‐agelasidine A is achieved which exemplifies the practical use of this protocol in a synthetic setting.
AbstractList	Chiral sulfones are of great importance in medicinal chemistry and chemical synthesis. Efficient methods for preparing enantiomerically enriched sulfone‐containing molecules can therefore be of significant value; such methods, however, are uncommon. Herein, we report the first general palladium‐catalyzed sulfonylation of vinyl cyclic carbonates with sodium sulfinates. A series of enantiomerically enriched tertiary allylic sulfones were synthesized in good yields with excellent enantiomeric ratios. Both aliphatic‐ and aryl‐substituted vinyl cyclic carbonates are suitable reactants with excellent results. This reaction features broad substrates scope, readily available starting materials, excellent regio‐ and enantioselectivity, and synthesis of sulfone‐bearing quaternary carbon stereocenters. Through the sulfonylation of geranyl derived cyclic carbonate 1 h , we achieve the formal total synthesis of (+)‐agelasidine A. Chiral sulfones are of great importance in medicinal chemistry and chemical synthesis. Efficient methods for preparing enantiomerically enriched sulfone-containing molecules can therefore be of significant value; such methods, however, are uncommon. Herein, we report the first general palladium-catalyzed sulfonylation of vinyl cyclic carbonates with sodium sulfinates. A series of enantiomerically enriched tertiary allylic sulfones were synthesized in good yields with excellent enantiomeric ratios. Both aliphatic- and aryl-substituted vinyl cyclic carbonates are suitable reactants with excellent results. This reaction features broad substrates scope, readily available starting materials, excellent regio- and enantioselectivity, and synthesis of sulfone-bearing quaternary carbon stereocenters. Through the sulfonylation of geranyl derived cyclic carbonate 1 h, we achieve the formal total synthesis of (+)-agelasidine A. Chiral sulfones are of great importance in medicinal chemistry and chemical synthesis. Efficient methods for preparing enantiomerically enriched sulfone‐containing molecules can therefore be of significant value; such methods, however, are uncommon. Herein, we report the first general palladium‐catalyzed sulfonylation of vinyl cyclic carbonates with sodium sulfinates. A series of enantiomerically enriched tertiary allylic sulfones were synthesized in good yields with excellent enantiomeric ratios. Both aliphatic‐ and aryl‐substituted vinyl cyclic carbonates are suitable reactants with excellent results. This reaction features broad substrates scope, readily available starting materials, excellent regio‐ and enantioselectivity, and synthesis of sulfone‐bearing quaternary carbon stereocenters. Through the sulfonylation of geranyl derived cyclic carbonate 1 h, we achieve the formal total synthesis of (+)‐agelasidine A. The first general example of regio‐ and enantioselective palladium catalyzed allylic sulfonylation of vinyl cyclic carbonates provides an efficient and direct way to construct sulfone‐bearing quaternary carbon stereocenters. A three steps formal total synthesis of (+)‐agelasidine A is achieved which exemplifies the practical use of this protocol in a synthetic setting. Chiral sulfones are of great importance in medicinal chemistry and chemical synthesis. Efficient methods for preparing enantiomerically enriched sulfone-containing molecules can therefore be of significant value; such methods, however, are uncommon. Herein, we report the first general palladium-catalyzed sulfonylation of vinyl cyclic carbonates with sodium sulfinates. A series of enantiomerically enriched tertiary allylic sulfones were synthesized in good yields with excellent enantiomeric ratios. Both aliphatic- and aryl-substituted vinyl cyclic carbonates are suitable reactants with excellent results. This reaction features broad substrates scope, readily available starting materials, excellent regio- and enantioselectivity, and synthesis of sulfone-bearing quaternary carbon stereocenters. Through the sulfonylation of geranyl derived cyclic carbonate 1 h, we achieve the formal total synthesis of (+)-agelasidine A.Chiral sulfones are of great importance in medicinal chemistry and chemical synthesis. Efficient methods for preparing enantiomerically enriched sulfone-containing molecules can therefore be of significant value; such methods, however, are uncommon. Herein, we report the first general palladium-catalyzed sulfonylation of vinyl cyclic carbonates with sodium sulfinates. A series of enantiomerically enriched tertiary allylic sulfones were synthesized in good yields with excellent enantiomeric ratios. Both aliphatic- and aryl-substituted vinyl cyclic carbonates are suitable reactants with excellent results. This reaction features broad substrates scope, readily available starting materials, excellent regio- and enantioselectivity, and synthesis of sulfone-bearing quaternary carbon stereocenters. Through the sulfonylation of geranyl derived cyclic carbonate 1 h, we achieve the formal total synthesis of (+)-agelasidine A.
Author	Zhao, Heng Khan, Shahid Khan, Ajmal Zhao, Depeng Zhang, Meina
Author_xml	– sequence: 1 givenname: Ajmal orcidid: 0000-0002-2415-7534 surname: Khan fullname: Khan, Ajmal email: ajmalkhan@xjtu.edu.cn organization: Xi'an Jiao Tong University – sequence: 2 givenname: Heng surname: Zhao fullname: Zhao, Heng organization: Sun Yat-sen University – sequence: 3 givenname: Meina surname: Zhang fullname: Zhang, Meina organization: Xi'an Jiao Tong University – sequence: 4 givenname: Shahid surname: Khan fullname: Khan, Shahid organization: Xi'an Jiao Tong University – sequence: 5 givenname: Depeng orcidid: 0000-0002-3058-9958 surname: Zhao fullname: Zhao, Depeng email: zhaodp5@mail.sysu.edu.cn organization: Sun Yat-sen University
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Snippet	Chiral sulfones are of great importance in medicinal chemistry and chemical synthesis. Efficient methods for preparing enantiomerically enriched...
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SubjectTerms	Aliphatic compounds allylic substitution Aromatic compounds asymmetric catalysis Carbon Carbonates Chemical synthesis Chemistry Chemistry, Multidisciplinary cyclic carbonates Enantiomers Organic chemistry Palladium Physical Sciences Science & Technology Sodium Substitution reactions Substrates Sulfones tertiary sulfones
Title	Regio‐ and Enantioselective Synthesis of Sulfone‐Bearing Quaternary Carbon Stereocenters by Pd‐Catalyzed Allylic Substitution
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