Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes

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2015-09-01
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Johnson, Kirsten
Schmidt, Adam
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Stanley, Levi
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Chemistry

The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).

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The Department of Chemistry was founded in 1880.

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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).

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

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Thu Jan 01 00:00:00 UTC 2015
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