Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes

The 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 co...

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Bibliographic Details
Published in:Organic letters 2015-10, Vol.17 (19), p.4654-4657
Main Authors: Johnson, Kirsten F, Schmidt, Adam C, Stanley, Levi M
Format: Article
Language:English
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Summary:The 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).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02559