60533-01-9Relevant articles and documents
A 1,3,2-Diazaphospholene-Catalyzed Reductive Claisen Rearrangement
Reed, John H.,Donets, Pavel A.,Miaskiewicz, Solène,Cramer, Nicolai
supporting information, p. 8893 - 8897 (2019/05/28)
1,3,2-Diazaphospholenes (DAPs) are an emerging class of organic hydrides. In this work, we exploited them as efficient catalysts for very mild reductive Claisen rearrangements. The method is tolerant towards a wide variety of functional groups and operates at ambient temperature. Besides being enantiospecific for substrates with existing stereogenic centers, the diastereoselectivity can be switched by varying solvents and DAP catalysts. The reaction kinetics show direct rearrangements of O-bound phospholene enolates and provide a proof-of-principle for catalytic enantioselective reactions.
A new variant of Reformatsky-Claisen rearrangement mediated by indium chloride
Ishihara, Jun,Koyama, Noriko,Nishino, Yukihiro,Takahashi, Keisuke,Hatakeyama, Susumi
scheme or table, p. 2351 - 2355 (2009/12/25)
A new variant of Reformatsky - Claisen rearrangement is described. The reaction of an allyl a-bromo ester in the presence of indium(I) chloride provides a general entry into the functionalized synthon. Georg Thieme Verlag Stuttgart.
A two-step, catalytic synthesis of δ-hydroxy-γ-lactones from allylic acetates and bis(trimethylsilyl)ketene acetals
Rudler, Henri,Parlier, Andree,Cantagrel, Frederic,Harris, Paul,Bellassoued, Moncef
, p. 771 - 772 (2007/10/03)
Bis(trimethylsilyl) ketene acetals react successively with allylic acetates, in the presence of Pd(0) then with H2O2, in the presence of methyltrioxorhenium, to give δ-hydroxy-γ-lactones via γ-unsaturated carboxylic acids.