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001 978-4-431-54231-5
003 DE-He213
005 20140220082926.0
007 cr nn 008mamaa
008 130125s2013 ja | s |||| 0|eng d
020 _a9784431542315
_9978-4-431-54231-5
024 7 _a10.1007/978-4-431-54231-5
_2doi
050 4 _aQD415-436
072 7 _aPNN
_2bicssc
072 7 _aSCI013040
_2bisacsh
082 0 4 _a547
_223
100 1 _aInokuma, Tsubasa.
_eauthor.
245 1 0 _aDevelopment of Novel Hydrogen-Bond Donor Catalysts
_h[electronic resource] /
_cby Tsubasa Inokuma.
264 1 _aTokyo :
_bSpringer Japan :
_bImprint: Springer,
_c2013.
300 _aXIV, 107 p. 76 illus., 7 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 _aIntroduction -- Development of HB donor catalysts -- Development and properties of novel HB donor catalysts -- Asymmetric Michael addition to alpha,beta-unsaturated imides catalyzed by HB donors -- Asymmetric Hydrazination of activated methylene compounds catalyzed by HB donors -- Development of hydroxy thiourea catalysts -- Asymmetric Michael addition of gamma-hydroxyenones and alkenylboronic acids -- Asymmetric Petasis Reaction of N-aryl-alpha-iminoamides and Alkenylboronates -- Conclusion.
520 _aThis work describes novel, effective hydrogen-bond (HB) donor catalysts based on a known bifunctional tertiary amine-thiourea, a privileged structure, which has been proven to be one of the most widely used organocatalysts. These HB donor catalysts derived from quinazoline and benzothiadiazine were initially synthesized as novel HB donors with their HB-donating abilities being measured by analytical methods. They were found to be effective for a variety of asymmetric transformations including Michael reactions of a, b-unsaturated imides and hydrazination reactions of 1,3-dicarbonyl compounds. Thiourea catalysts that have an additional functional group are also described. Specifically, thioureas that bear a hydroxyl group were synthesized and subsequently used as novel bifunctional organocatalysts for catalytic, asymmetric Petasis-type reactions involving organoboronic acids as nucleophiles. These addition reactions were difficult to achieve using existing organocatalysts. One of the developed catalytic methods can be applied to the synthesis of biologically interesting peptide-derived compounds possessing unnatural vinyl glycine moieties. These findings introduce new criteria required for the development of organocatalysts for asymmetric reactions, thus making a significant contribution to the field of organocatalysis.
650 0 _aChemistry.
650 0 _aChemistry, Organic.
650 0 _aBiochemistry.
650 0 _aCatalysis.
650 1 4 _aChemistry.
650 2 4 _aOrganic Chemistry.
650 2 4 _aMedicinal Chemistry.
650 2 4 _aCatalysis.
710 2 _aSpringerLink (Online service)
773 0 _tSpringer eBooks
776 0 8 _iPrinted edition:
_z9784431542308
830 0 _aSpringer Theses, Recognizing Outstanding Ph.D. Research,
_x2190-5053
856 4 0 _uhttp://dx.doi.org/10.1007/978-4-431-54231-5
912 _aZDB-2-CMS
999 _c99057
_d99057