Propargylic alcohols and their derivatives are important classes of organic compounds that can be easily accessible from terminal alkynes and aldehydes or ketones. They are attractive and have been extensively applied as synthetic intermediates in modern organic synthesis. Recent investigations on the chemistry of propargylic alcohols and their derivatives disclosed a variety of highly efficient Lewis acid-catalyzed cascade reactions based on Meyer−Schuster rearrangement of propargylic alcohols and [3,3] rearrangement of propargylic esters and propargyl vinyl ethers. A tremendous number of structurally versatile enones, carbocycles, and heterocycles have been constructed through these methodologies. These advances, including our recent researches in this field, are summarized in this review.
A new class of chiral phosphoric acids with spirobiindane as scaffold were conveniently synthesized from (S)-1,1'-spirobiindane-7,7'-diol ((S)-SPINOL) and employed to catalyze the asymmetric Friedel-Crafts reaction of indoles with imines to afford 3-indolyl methanamines. High yields (68-97%) and excellent enantioselectivities (up to 99% ee) were obtained.
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