17046-02-5Relevant articles and documents
From enantiopure hydroxyaldehydes to complex heterocyclic scaffolds: Development of domino Petasis/diels-alder and cross-metathesis/Michael addition reactions
Cannillo, Alexandre,Norsikian, Stéphanie,Tran Huu Dau, Marie-Elise,Retailleau, Pascal,Iorga, Bogdan I.,Beau, Jean-Marie
, p. 12133 - 12143 (2014)
One-step assembly of hexahydroisoindole scaffolds by a sequence that combines the Petasis (borono-Mannich) and Diels-Alder reactions is described. The unique selectivity observed experimentally was confirmed by quantum calculations. The current method is
A novel approach to γ-hydroxy-α,β-unsaturated compounds
Krawczyk, Henryk,Wasek, Katarzyna,Kedzia, Jacek
experimental part, p. 3299 - 3306 (2009/05/11)
A simple synthesis of (E)-alk-1-enyl mesylates from (E)-alk-1- enylphosphonates is reported. Construction of γ-hydroxy-α,β- unsaturated compounds was achieved by a two-step process involving dihydroxylation of the enol mesylates followed by HWE reaction of the resulting α-hydroxy aldehydes with activated methylphosphonates. Enantioselective synthesis of the title compounds is also reported.
Synthesis of Trimethylsilyloxy and Hydroxy Compounds from Carbanions and Bis(trimethylsilyl)peroxide.
Camici, Lucia,Dembech, Pasquale,Ricci, Alfredo,Seconi, Giancarlo,Taddei, Maurizio
, p. 4197 - 4206 (2007/10/02)
The reactions of bis(trimethylsilyl)peroxide with alkyl, vinyl, alkynyl, aromatic and heteroaromatic anions are described.Depending on the reaction conditions, the trimethylsilyloxy derivatives can be obtained alone or together with the corresponding trimethylsilyl derivatives, which is sometimes the major product.Enolates, generated using magnesium diisopropylamide give the corresponding hydroxycarbonyl compounds in good yields.An attempt to rationalise the above results is given, emphasising the wide use of bis(trimethylsilyl)peroxide in organic synthesis as an electrophilic hydroxylation reagent.
