Enantioselective C–H Arylation and Vinylation of Cyclobutyl Carboxylic Amides

Chiral mono-N-protected aminomethyl oxazoline (MPAO) ligands are found to promote enantioselective C–H arylation and vinylation of the cyclobutyl carboxylic acid derivatives via Pd­(II)/Pd­(IV) redox catalysis. This ligand scaffold overcame two important limitations of the previous MPAHA (mono-N-pro...

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Published inACS catalysis Vol. 8; no. 3; pp. 2577 - 2581
Main Authors Wu, Qing-Feng, Wang, Xiao-Bing, Shen, Peng-Xiang, Yu, Jin-Quan
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 02.03.2018
Subjects
MPAO ligands
vinylation
cyclobutanes
α-hydrogen atom
C−H activation
C–H activation
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Summary:Chiral mono-N-protected aminomethyl oxazoline (MPAO) ligands are found to promote enantioselective C–H arylation and vinylation of the cyclobutyl carboxylic acid derivatives via Pd­(II)/Pd­(IV) redox catalysis. This ligand scaffold overcame two important limitations of the previous MPAHA (mono-N-protected α-amino-O-methylhydroxamic acid) ligand-enabled asymmetric C–H activation/C–C coupling reactions of cyclic carboxylic amides through Pd­(II)/Pd(0) catalysis: substrates containing α-hydrogen atoms are not compatible, and vinylation has not been developed. Sequential C–H arylation and vinylation of cyclobutanes are also performed to construct three contiguous chiral centers on the crowded cyclobutane rings, rendering this reaction highly versatile for the preparation of chiral cyclobutanes.
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Author Contributions. Q.W, & X.W. contributed equally to this work.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b00069