Details

Autor(en) / Beteiligte

• Craig, Robert A
• Loskot, Steven A
• Mohr, Justin T
• Behenna, Douglas C
• Harned, Andrew M
• Stoltz, Brian M

Titel

Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones

Ist Teil von

• Organic letters, 2015-11, Vol.17 (21), p.5160-5163

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2015

Quelle

MEDLINE

Beschreibungen/Notizen

• The first general method for the enantioselective construction of all-carbon quaternary centers on cyclopentanones by enantioselective palladium-catalyzed decarboxylative allylic alkylation is described. Employing the electronically modified (S)-(p-CF3)3-t-BuPHOX ligand, α-quaternary cyclopentanones were isolated in yields up to >99% with ee’s up to 94%. Additionally, in order to facilitate large-scale application of this method, a low catalyst loading protocol was employed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.