A highly enantio- and diastereoselective catalytic intramolecular Stetter reaction.
A highly enantio- and diastereoselective intramolecular Stetter reaction has been developed. Subjection of alpha,alpha-disubstituted Michael acceptors to an asymmetric intramolecular Stetter reaction results in a highly enantioselective conjugate addition and a diastereoselective proton transfer. Available evidence suggests the diastereoselective protonation occurs via intramolecular delivery to the sterically more hindered face of the enolate. The scope of the trisubstituted Michael acceptors has been examined and found to be broad with respect to the size of the alpha-substituent and nature of the Michael acceptor. Aliphatic and aromatic aldehydes were examined and found to afford the desired product in good overall yield with high enantio- and diastereoselectivity.
Read de Alaniz
Javier
J
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Rovis
Tomislav
T
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000737:chemistry; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis*; D055672:Static Electricity; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry
D000447:Aldehydes; D000475:Alkenes; D002839:Chromans; D004988:Ethers, Cyclic; D007659:Ketones; D014230:Triazoles