Asymmetric cyclopropane synthesis via phosphine oxide mediated cascade reactions.
A silyloxy-THF has been converted into a cyclopropane containing three stereocentres as mixture of diastereoisomers. The mechanism of the reaction has been established and the source of stereochemical leakage proposed. An alternative stereospecific cascade reaction has been discovered.
Boesen
Thomas
T
University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK.
Fox
David J
DJ
Galloway
Warren
W
Pedersen
Daniel Sejer
DS
Tyzack
Charles R
CR
Warren
Stuart
S
D003521:Cyclopropanes / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D003521:Cyclopropanes; D005663:Furans; D010720:Phosphines; D012821:Silanes