title: Stereoselective cross aldol condensation of bicyclo[3.2.0]alkanones.
abstract: A cross aldol reaction between [(S)-(-)] or [(R)-(+)]-benzyloxypropanal and silyl enol ethers derived from bicyclo[3.2.0]alkanones was carried out in the presence of TiCl4, leading with total stereoselectivity to a 1 : 1 mixture of enantiomerically pure diastereomers isolated in 81% overall yield. Thus, 5 stereogenic centers could be created starting from one. Furthermore, an efficient access to an enantiomerically pure tricyclo[5.3.0.0(2,6)]decane scaffold was possible via a 4 step reaction sequence.
authors: Université de Strasbourg, Institut de Chimie, UMR UdS/CNRS 7177, Laboratoire de Chimie Organique Synthétique, 1 rue Blaise Pascal, BP 296/R8, 67008 Strasbourg-Cedex, France. lmiesch@unistra.fr
authors: Laurence
authors: L
authors: Miesch
authors: Tania
authors: T
authors: Welsch
authors: Michel
authors: M
authors: Miesch
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004987:Ethers; D007659:Ketones