In:
Angewandte Chemie International Edition, Wiley, Vol. 60, No. 14 ( 2021-03-29), p. 7913-7919
Kurzfassung:
The use of functionalized aldimines has been demonstrated as newly structural 1,4‐dipole precursors under carbene catalysis. More importantly, enantiodivergent organocatalysis has been successfully developed using carbene catalysts with the same absolute configuration, leading to both ( R )‐ and ( S )‐ enantiomers of six‐membered heterocycles with quaternary carbon centers. This strategy features a broad substrate scope, mild reaction conditions, and good enantiomeric ratio. DFT calculation results indicated that hydrogen bond C−H⋅⋅⋅F interactions between the catalyst and substrate are the key factors for controlling and even switching the enantioselectivity. These new 1,4‐dipoles can also react with isatin and its imines under carbene catalysis, allowing for access to the spiro oxindoles with excellent enantiomeric ratios.
Materialart:
Online-Ressource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.202017017
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2021
ZDB Id:
2011836-3
ZDB Id:
123227-7
