Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes

Supplemental Files
Date
2015-09-01
Authors
Johnson, Kirsten
Schmidt, Adam
Stanley, Levi
Journal Title
Journal ISSN
Volume Title
Publisher
Altmetrics
Authors
Research Projects
Organizational Units
Chemistry
Organizational Unit
Journal Issue
Series
Abstract

The development of a rhodium catalyst for endo- and enantioselective hydroacylation ofortho-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).

Description

Reprinted (adapted) with permission from Organic Letters 17 (2015): 4654, doi:10.1021/acs.orglett.5b02559. Copyright 2015 American Chemical Society.

Keywords
Citation
DOI
Collections