941576-68-7Relevant academic research and scientific papers
Catalytic enantio- and diastereoselective formation of β-sultones: Ring-strained precursors for enantioenriched β-hydroxysulfonyl derivatives
Koch, Florian M.,Peters, Rene
, p. 2685 - 2689 (2007)
(Chemical Equation Presented) Sultones swing! Sulfenes, the highly reactive sulfonyl equivalents of ketenes, were used for the first time as substrates in asymmetric catalysis. A [2+2] cyclo-cyclocondensation reaction catalyzed by a tertiary amine enabled
Lewis acid/base catalyzed [2+2]-cycloaddition of sulfenes and aldehydes: A versatile entry to chiral sulfonyl and sulfinyl derivatives
Koch, Florian M.,Peters, Rene
supporting information; experimental part, p. 3679 - 3692 (2011/05/05)
The first catalytic asymmetric synthesis of β-sultones is reported. This development has enabled a rapid access to a number of highly enantioenriched biologically interesting sulfonyl and sulfinyl compound classes, which makes use of the inherent ring strain of the four-membered heterocycles. The products possess either two vicinal stereocenters, such as in β-hydroxy-sulfonamides, -sulfonates, -sulfones, -sulfonic acids, -sulfinic acids, γ-sultines, and γ-sultones or a single stereocenter, such as in α-branched alkyl or allyl sulfonic acids. This work also represents the first application of sulfene intermediates in asymmetric catalysis. The reactivity of a sulfene normally acting as an electrophile could be reverted by the formation of a nucleophilic zwitterionic sulfene-amine adduct. To achieve a combination of high enantioselectivity and reactivity, cooperative catalytic action of a chiral nucleophilic tertiary amine (the cinchona alkaloid derivative diydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether ((DHQ)2PYR)) and Bi(OTf)3 or In(OTf)3 was of primary importance.
