ol5b02559_si_001.pdf (20.55 MB)
Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes
journal contribution
posted on 2015-10-02, 00:00 authored by Kirsten
F. Johnson, Adam C. Schmidt, Levi M. StanleyThe
development of a rhodium catalyst for endo- and enantioselective
hydroacylation of ortho-allylbenzaldehydes
is reported. A catalyst generated in situ from [Rh(COD)Cl]2, (R)-DTBM-SEGPHOS, and NaBARF promotes the
desired hydroacylation reactions and minimizes the formation of byproducts
from competitive alkene isomerization and ene/dehydration pathways.
These rhodium-catalyzed processes generate the 3,4-dihydronaphthalen-1(2H)-one products in moderate-to-high yields (49–91%)
with excellent enantioselectivities (96–99% ee).