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An Efficient, Facile, and General Stereoselective Synthesis of Heterosubstituted Alkylidenecyclopropanes
Author(s) -
Masarwa Ahmad,
Stanger Am,
Marek Ilan
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200702713
Subject(s) - stereoselectivity , chemistry , combinatorial chemistry , organic chemistry , catalysis
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. R 1 , R 2 =alkyl, aryl.