Copper-Catalyzed Enantioselective 1,2-Allylation of Azadienes with Allylboronates DOI

Zhi-Hong Dong,

Shu Li, Teng Long

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3235 - 3240

Published: April 1, 2024

Catalytic asymmetric 1,2-allylation of aurone-derived azadienes is very difficult to achieve due the driving force for aromatization and greater steric hindrance 1,2-addition compared with 1,4-addition. By taking advantage ability nitrogen ligated metal complexes, we successfully demonstrated first example copper-catalyzed allylboronates highly enantioselective synthesis homoallylic amines. Meanwhile, enantioenriched 1,4-addition products could also be obtained through a subsequent 3,3-sigmatropic rearrangement products. Extensive DFT calculations were carried out elucidate origins high regioselectivity (1,2- vs 1,4-) enantioselectivity.

Language: Английский

Copper-Catalyzed Enantioselective 1,2-Allylation of Azadienes with Allylboronates DOI

Zhi-Hong Dong,

Shu Li, Teng Long

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3235 - 3240

Published: April 1, 2024

Catalytic asymmetric 1,2-allylation of aurone-derived azadienes is very difficult to achieve due the driving force for aromatization and greater steric hindrance 1,2-addition compared with 1,4-addition. By taking advantage ability nitrogen ligated metal complexes, we successfully demonstrated first example copper-catalyzed allylboronates highly enantioselective synthesis homoallylic amines. Meanwhile, enantioenriched 1,4-addition products could also be obtained through a subsequent 3,3-sigmatropic rearrangement products. Extensive DFT calculations were carried out elucidate origins high regioselectivity (1,2- vs 1,4-) enantioselectivity.

Language: Английский

Citations

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