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Highly enantioselective synthesis of α-tertiary chiral amino acid derivatives through rhodium-catalyzed asymmetric arylation of cyclic N-sulfonyl α-ketimino esters

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Abstract

By employing an easily available, exceptionally simple sulfur-olefin ligand, a highly enantioselective rhodium-catalyzed arylation of cyclic N-sulfonyl α-ketimino esters with arylboronic acids has been developed. The reaction allows facile access to a wide range of α,α-gem-diaryl substituted chiral amino esters in excellent yields with extremely high enantioselectivities (uniformly 98–99% ee). The synthetic utility of this approach was highlighted by the efficient synthesis of a series of interesting molecules including unique chiral spirocycles bearing 2,3-dihydrobenzofuran and 1H-isoindole skeletons.

Graphical abstract: Highly enantioselective synthesis of α-tertiary chiral amino acid derivatives through rhodium-catalyzed asymmetric arylation of cyclic N-sulfonyl α-ketimino esters

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Publication details

The article was received on 10 Apr 2018, accepted on 05 May 2018 and first published on 07 May 2018


Article type: Paper
DOI: 10.1039/C8OB00840J
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Highly enantioselective synthesis of α-tertiary chiral amino acid derivatives through rhodium-catalyzed asymmetric arylation of cyclic N-sulfonyl α-ketimino esters

    Z. Wang and M. Xu, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00840J

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