253304-53-9Relevant academic research and scientific papers
Catalytic asymmetric synthesis of axially chiral o-iodoanilides by phase-transfer catalyzed alkylations
Shirakawa, Seiji,Liu, Kun,Maruoka, Keiji
, p. 916 - 919 (2012)
Catalytic asymmetric synthesis of axially chiral o-iodoacrylanilides and N-allyl-o-iodoanilides as useful chiral building blocks was achieved via chiral quaternary ammonium salt-catalyzed N-alkylations under phase-transfer conditions. The transition-state structure for the present reaction is discussed on the basis of the X-ray crystal structure of ammonium anilide.
Asymmetric radical cyclization reactions of axially chiral N-allyl-o-iodoanilides to form enantioenriched N-acyl dihydroindoles
Curran, Dennis P.,Chen, Christine H.-T.,Geib, Steven J.,Lapierre, Andre J. B.
, p. 4413 - 4424 (2007/10/03)
Radical cyclizations of enantiomerically enriched N-allyl-o-iodoanilides provide N-acyl-3-alkyl-2,3-dihydroindoles in good yields and with good to excellent levels of chirality transfer from the N-Ar axis to the new stereocenter. In competitive cyclizations of N-acryloyl-N-allyl-o-iodoanilides, the addition of an o-methyl group reverses the regioselectivity of the radical cyclization from the acryloyl group to the allyl group. Approximate rate constants for representative radical cyclizations have been measured to provide insight into the origin of these observations.
