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Article
Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes
Organic Letters
  • Kirsten F. Johnson, Iowa State University
  • Adam C. Schmidt, Iowa State University
  • Levi M. Stanley, Iowa State University
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
9-1-2015
DOI
10.1021/acs.orglett.5b02559
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).
Comments

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

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Kirsten F. Johnson, Adam C. Schmidt and Levi M. Stanley. "Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes" Organic Letters Vol. 17 Iss. 19 (2015) p. 4654 - 4657
Available at: http://works.bepress.com/levi_stanley/1/