Triflimide-catalyzed allylsilane annulations of benzylic alcohols for the divergent synthesis of indanes and tetralins

Abstract

The development of a triflimide-catalyzed annulation of benzylic alcohols with allylsilanes for the divergent synthesis of indane or tetralin structures from common precursors is reported.

Scope and advances in the catalytic propargylic substitution reaction

“…Several studies on coupling of allylic and benzylic alcohols with allylsilanes have appeared, using various Lewis and Brønsted acids, namely BiCl 3 , ZrCl 4 , ion-exchanged montmorillonite, phosphomolybdic acid, FeCl 3 $6H 2 O, and HN(SO 2 F) 2 . 222,223 Despite the availability of these earlier methods, development of environmentally benign efficient processes that employ readily available catalysts in combination with non-volatile solvents that can be recycled and reused is highly desirable.…”

Chemical constituents from the stems of Machilus philippinensis Merr. and the neuroprotective activity of cinnamophilin

“…53 However, with careful evaluation of all the 1 H and 13 C NMR data (Table 3), it should be revised as dehydroguaiaretic acid (9) which had already been published in the literature. 23,54 The plausible biosynthetic mechanism of above-mentioned new lignans was proposed as shown (Fig. 3).…”

Triflimide: An Overlooked High‐Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones

“…Triflimide [HNTf 2 : bis(trifluoromethanesulfonyl)imide] is a useful strong acid catalyst (p K a =0.3 in MeCN) for various transformations, including aldol reactions, cycloadditions, allylations, Friedel–Crafts reactions, Nazarov cyclizations, Michael additions, Mannich reactions,, [3,3]‐sigmatropic rearrangements and others . The Yamamoto group has investigated ketone‐derived trialkyl‐silyl‐enol ethers, or aldehyde‐derived tris(trimethylsilyl)silyl “super silyl” enol ethers for the synthesis of β‐siloxy aldehydes by the Mukaiyama aldol reaction.…”