TY - JOUR
T1 - An efficient, facile, and general stereoselective synthesis of heterosubstituted alkylidenecyclopropanes
AU - Masarwa, Ahmad
AU - Stanger, Amnon
AU - Marek, Ilan
PY - 2007
Y1 - 2007
N2 - (Chemical Equation Presented) With just a nudge (in the form of silica gel, an acidic ion-exchange resin, or heating at about 40°C), the acetate derivatives of enantiomerically enriched cyclopropenyl alcohols undergo sigmatropic rearrangement to give alkylidenecyclopropanes with high ee values (see scheme). Similarly, the rearrangement of phosphinite derivatives at room temperature leads to phosphine oxide precursors of unusual chiral phosphine ligands. R1, R2 = alkyl, aryl.
AB - (Chemical Equation Presented) With just a nudge (in the form of silica gel, an acidic ion-exchange resin, or heating at about 40°C), the acetate derivatives of enantiomerically enriched cyclopropenyl alcohols undergo sigmatropic rearrangement to give alkylidenecyclopropanes with high ee values (see scheme). Similarly, the rearrangement of phosphinite derivatives at room temperature leads to phosphine oxide precursors of unusual chiral phosphine ligands. R1, R2 = alkyl, aryl.
KW - Alkylidenecyclopropanes
KW - Chiral phosphanes
KW - Cyclopropenes
KW - Sigmatropic rearrangement
KW - Synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=35648951167&partnerID=8YFLogxK
U2 - 10.1002/anie.200702713
DO - 10.1002/anie.200702713
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C2 - 17854109
AN - SCOPUS:35648951167
SN - 1433-7851
VL - 46
SP - 8039
EP - 8042
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 42
ER -