Tetrasubstituted aldehydes through electronic and strain-controlled branch-selective stereoselective hydroformylation
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1
University of Wisconsin-Madison, United States
Hydroformylation is a convenient and atom-economical strategy to introduce useful aldehyde functionality into simple alkene building blocks. In addition, hydroformylation is the largest industrial process for the synthesis of commodity chemicals (18 billion pounds per year). While there has been significant progress in the asymmetric hydroformylation (AHF) of 1,1'-disubstituted and 1,1′,2-trisubstituted alkenes, general methods to achieve predictable, regiocontrolled AHF of 1,1'-disubstituted and 1,1′,2-trisubstituted alkenes to deliver α-tetrasubstituted aldehydes are lacking. Current results suggests that sterics, electronics, and ring strain can be harnessed to provide ready access to valuable α-tetrasubstituted aldehyde synthetic building blocks by promoting branched-selective hydroformylation. The ligand identity is key to achieving high regioselectivity, while the mild reaction conditions minimize competing side products.
Acknowledgements
Clark R. Landis
Jennifer M. Schomaker
Floriana Foarta
Keywords:
α‑Tetrasubstituted Aldehydes,
Branch-selective hydroformylation,
1,1'-Disubstituted alkene,
1,1′,2-Trisubstituted Alkene,
Hydroformylation catalyst
Conference:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference , Orlando, Florida, United States, 17 Sep - 20 Sep, 2018.
Presentation Type:
Oral Presentation
Topic:
Organic Chemistry
Citation:
Eshon
J,
Schomaker
JM,
Landis
CR and
Foarta
F
(2019). Tetrasubstituted aldehydes through electronic and strain-controlled branch-selective stereoselective hydroformylation.
Front. Chem.
Conference Abstract:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference .
doi: 10.3389/conf.fchem.2018.01.00023
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Received:
08 Oct 2018;
Published Online:
17 Jan 2019.
*
Correspondence:
Ms. Josephine Eshon, University of Wisconsin-Madison, Madison, Alabama, 53715-1149, United States, lovejosephine93@yahoo.com
Mrs. Jennifer M Schomaker, University of Wisconsin-Madison, Madison, Alabama, 53715-1149, United States, schomakerj@chem.wisc.edu
Mr. Clark R Landis, University of Wisconsin-Madison, Madison, Alabama, 53715-1149, United States, landis@chem.wisc.edu
Mrs. Floriana Foarta, University of Wisconsin-Madison, Madison, Alabama, 53715-1149, United States, floriana.foarta@gmail.com