Year: 2007
Type: editorial
Abstract: Significance The authors report a direct enantioselective allylic alkylation of aldehydes using SOMO activation. They recognized that a one-electron oxidation of a transient enamine species would generate a 3π-electron radical cation with a singly occupied molecular orbital (SOMO) that is activated to a variety of π-rich nucleophiles. Imidazolidinium salt 1 was found to be the best catalyst and ceric ammonium nitrate (CAN) was used as the stoichiometric oxidant for the allylic alkylation of different aldehydes. With 20 mol% of the catalyst 1 and two equivalents of CAN, good to high yields (72-88%) and high enantioselectivities (ee = 93:7 to 98:2) are obtained for a variety of allylsilanes.
Source: Synfacts
Authors: T. D. Beeson, A. Mastracchio, J.-B. Hong, K. Ashton, D. W. C. Macmillan
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W2125750893