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. 2018 Mar 2;8(3):2577-2584.
doi: 10.1021/acscatal.8b00069. Epub 2018 Feb 5.

Enantioselective C-H Arylation and Vinylation of Cyclobutyl Carboxylic Amides

Qing-Feng Wu  1 , Xiao-Bing Wang  1 , Peng-Xiang Shen  1 , Jin-Quan Yu  1
Affiliations

Enantioselective C-H Arylation and Vinylation of Cyclobutyl Carboxylic Amides

Qing-Feng Wu et al. ACS Catal. .

Abstract

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) ligands-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; vinylation has not been developed. Sequential C-H arylation and vinylation of cyclobutanes are also accomplished to construct three consecutive chiral centers on the crowded cyclobutane rings, rendering this reaction highly versatile for the preparation of chiral cyclobutanes.

Keywords: C–H activation; MPAO ligands; cyclobutanes; vinylation; α-hydrogen atom.

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Conflict of interest statement

Notes. The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Biologically Active Compounds Containing Cyclobutanes
Scheme 1
Scheme 1
Enantioselective C–H Functionalization of Cyclobutyl Carboxylic Amide
Scheme 2
Scheme 2
Proposed Catalytic Cycle
Scheme 3
Scheme 3
Diversification of the Chiral Cyclobutanes
Scheme 4
Scheme 4
Removal of the amide auxiliary
See this image and copyright information in PMC

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