The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas.
Intramolecular carbonyl ene reactions of highly activated enophiles can be catalysed by H-bonding thio-ureas to give tertiary alcohols in high yields without extensive isomerisation side products. An asymmetric variant of this reaction was realised using a chiral thiourea but was limited by low enantioselectivity (up to 33% e.e.) and low turnover frequencies.
Clarke
Matthew L
ML
School of Chemistry, University of St, Andrews, EaStCHEM, St, Andrews, Fife, KY16 9ST, UK. mc28@st-andrews.ac.uk
Jones
Charlotte E S
CE
France
Marcia B
MB