Design and Synthesis of C4‐Symmetric Axially Chiral β‐Aryl Porphyrins and Application for Supporting Ir(III)‐Catalyzed Enantioselective C−H Alkylation DOI

Shanshan Yuan,

Jun‐Chao Sun,

Xiaoming Zhao

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(28)

Published: April 29, 2024

Abstract A hitherto unknown class of C 4 ‐symmetric aryl −C β (C 3 , 8 13 18 ) axially chiral porphyrins has been synthesized and the application their iridium (Ir) complexes in catalytic asymmetric C(sp )−H functionalization is documented. Cyclotetramerization enantioenriched 2‐hydroxymethyl‐3‐naphthyl pyrroles under mild acidic conditions affords, after oxidation with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ), α,α,α,α‐atropenantiomer as an only isolable diastereomer. Both regioisomeric Ir(Por*)(CO)(Cl) catalyze carbene C−H insertion reaction affording same enantiomer, albeit slight difference enantioselectivity. With optimum Ir‐complex e 2‐substituted arylacetic acid derivatives were generated from diazo compounds cyclohexadiene excellent yields enantioselectivities.

Language: Английский

Design and Synthesis of C4‐Symmetric Axially Chiral β‐Aryl Porphyrins and Application for Supporting Ir(III)‐Catalyzed Enantioselective C−H Alkylation DOI

Shanshan Yuan,

Jun‐Chao Sun,

Xiaoming Zhao

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(28)

Published: April 29, 2024

A hitherto unknown class of C

Language: Английский

Citations

4
Design and Synthesis of C4‐Symmetric Axially Chiral β‐Aryl Porphyrins and Application for Supporting Ir(III)‐Catalyzed Enantioselective C−H Alkylation DOI

Shanshan Yuan,

Jun‐Chao Sun,

Xiaoming Zhao

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(28)

Published: April 29, 2024

Abstract A hitherto unknown class of C 4 ‐symmetric aryl −C β (C 3 , 8 13 18 ) axially chiral porphyrins has been synthesized and the application their iridium (Ir) complexes in catalytic asymmetric C(sp )−H functionalization is documented. Cyclotetramerization enantioenriched 2‐hydroxymethyl‐3‐naphthyl pyrroles under mild acidic conditions affords, after oxidation with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ), α,α,α,α‐atropenantiomer as an only isolable diastereomer. Both regioisomeric Ir(Por*)(CO)(Cl) catalyze carbene C−H insertion reaction affording same enantiomer, albeit slight difference enantioselectivity. With optimum Ir‐complex e 2‐substituted arylacetic acid derivatives were generated from diazo compounds cyclohexadiene excellent yields enantioselectivities.

Language: Английский

Citations

0