000 03723nam a22004815i 4500
001 978-3-642-28118-1
003 DE-He213
005 20140220083311.0
007 cr nn 008mamaa
008 120531s2012 gw | s |||| 0|eng d
020 _a9783642281181
_9978-3-642-28118-1
024 7 _a10.1007/978-3-642-28118-1
_2doi
050 4 _aQD415-436
072 7 _aPNN
_2bicssc
072 7 _aSCI013040
_2bisacsh
082 0 4 _a547
_223
100 1 _aReisinger, Corinna.
_eauthor.
245 1 0 _aEpoxidations and Hydroperoxidations of α,β-Unsaturated Ketones
_h[electronic resource] :
_bAn Approach through Asymmetric Organocatalysis /
_cby Corinna Reisinger.
264 1 _aBerlin, Heidelberg :
_bSpringer Berlin Heidelberg :
_bImprint: Springer,
_c2012.
300 _aXV, 257 p. 469 illus., 42 illus. in color.
_bonline resource.
336 _atext
_btxt
_2rdacontent
337 _acomputer
_bc
_2rdamedia
338 _aonline resource
_bcr
_2rdacarrier
347 _atext file
_bPDF
_2rda
490 1 _aSpringer Theses, Recognizing Outstanding Ph.D. Research,
_x2190-5053
505 0 _aBackground -- Asymmetric Organocatalysis -- Catalytic Asymmetric Epoxidation of Electron-Deficient Olefins -- Synthesis and Relevance of 3-Hydroxy-1,2-dioxolanes and 1,2-Dioxolanes -- Objectives of this Ph.D. Work -- Results and Discussion -- Catalytic Asymmetric Epoxidation of Cyclic Enones -- Catalytic Asymmetric Epoxidation and Hydroperoxidation of Acyclic Enones -- Synthetic Transformations of Optically Active a,ß-Epoxy Ketones and 3-Hydroxy-1,2-dioxolanes -- Summary and Conclusions -- Mechanistic Considerations -- Preparation of Starting Materials -- Catalyst Synthesis -- Summary -- Outlook -- Experimental Part -- General Experimental Conditions -- Catalytic Asymmetric Epoxidation of Cyclic Enones -- Catalytic Asymmetric Hydroperoxidation and Epoxidation of Acyclic Enones -- Synthetic Transformations of Optically Active Products -- Preparation of Starting Materials -- Catalyst Synthesis.
520 _aCorinna Reisinger has developed a new organocatalytic asymmetric epoxidation of cyclic and acyclic α,β-unsaturated ketones. In this thesis, Corinna documents her methodology, using primary amine salts as catalysts, and hydrogen peroxide as an inexpensive and environmentally benign oxidant. She describes the unprecedented and powerful catalytic asymmetric hydro­peroxi­dation of α,β-enones, a process which produces optically active five-membered cyclic peroxyhemiketals in a single operation. She also proves the versatility and synthetic value of the cyclic peroxyhemiketals by converting them into highly enantioenriched acyclic and cyclic aldol products. Currently, these cyclic aldol products are inaccessible by any other synthetic means. Furthermore, cyclic peroxyhemiketals are precursors to optically active 1,2-dioxolanes which are of biological relevance. This work is a breakthrough in the field of asymmetric epoxidation chemistry and outlines the most efficient method in the literature for generating highly enantioselective cyclic epoxyketones known to date.
650 0 _aChemistry.
650 0 _aChemistry, Organic.
650 0 _aChemical engineering.
650 0 _aCatalysis.
650 1 4 _aChemistry.
650 2 4 _aOrganic Chemistry.
650 2 4 _aCatalysis.
650 2 4 _aIndustrial Chemistry/Chemical Engineering.
710 2 _aSpringerLink (Online service)
773 0 _tSpringer eBooks
776 0 8 _iPrinted edition:
_z9783642281174
830 0 _aSpringer Theses, Recognizing Outstanding Ph.D. Research,
_x2190-5053
856 4 0 _uhttp://dx.doi.org/10.1007/978-3-642-28118-1
912 _aZDB-2-CMS
999 _c102731
_d102731