Cargando…

Development of Novel Hydrogen-Bond Donor Catalysts

This 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...

Descripción completa

Detalles Bibliográficos
Clasificación:Libro Electrónico
Autor principal: Inokuma, Tsubasa (Autor)
Autor Corporativo: SpringerLink (Online service)
Formato: Electrónico eBook
Idioma:Inglés
Publicado: Tokyo : Springer Japan : Imprint: Springer, 2013.
Edición:1st ed. 2013.
Colección:Springer Theses, Recognizing Outstanding Ph.D. Research,
Temas:
Acceso en línea:Texto Completo

MARC

LEADER 00000nam a22000005i 4500
001 978-4-431-54231-5
003 DE-He213
005 20220117132549.0
007 cr nn 008mamaa
008 130125s2013 ja | s |||| 0|eng d
020 |a 9784431542315  |9 978-4-431-54231-5 
024 7 |a 10.1007/978-4-431-54231-5  |2 doi 
050 4 |a QD241-441 
072 7 |a PNN  |2 bicssc 
072 7 |a SCI013040  |2 bisacsh 
072 7 |a PNN  |2 thema 
082 0 4 |a 547  |2 23 
100 1 |a Inokuma, Tsubasa.  |e author.  |4 aut  |4 http://id.loc.gov/vocabulary/relators/aut 
245 1 0 |a Development of Novel Hydrogen-Bond Donor Catalysts  |h [electronic resource] /  |c by Tsubasa Inokuma. 
250 |a 1st ed. 2013. 
264 1 |a Tokyo :  |b Springer Japan :  |b Imprint: Springer,  |c 2013. 
300 |a XIV, 107 p.  |b online resource. 
336 |a text  |b txt  |2 rdacontent 
337 |a computer  |b c  |2 rdamedia 
338 |a online resource  |b cr  |2 rdacarrier 
347 |a text file  |b PDF  |2 rda 
490 1 |a Springer Theses, Recognizing Outstanding Ph.D. Research,  |x 2190-5061 
505 0 |a Introduction -- 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 |a This 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 |a Chemistry, Organic. 
650 0 |a Medicinal chemistry. 
650 0 |a Catalysis. 
650 1 4 |a Organic Chemistry. 
650 2 4 |a Medicinal Chemistry. 
650 2 4 |a Catalysis. 
710 2 |a SpringerLink (Online service) 
773 0 |t Springer Nature eBook 
776 0 8 |i Printed edition:  |z 9784431542322 
776 0 8 |i Printed edition:  |z 9784431547457 
776 0 8 |i Printed edition:  |z 9784431542308 
830 0 |a Springer Theses, Recognizing Outstanding Ph.D. Research,  |x 2190-5061 
856 4 0 |u https://doi.uam.elogim.com/10.1007/978-4-431-54231-5  |z Texto Completo 
912 |a ZDB-2-CMS 
912 |a ZDB-2-SXC 
950 |a Chemistry and Materials Science (SpringerNature-11644) 
950 |a Chemistry and Material Science (R0) (SpringerNature-43709)