Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction

An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with alpha-chloroaldehydes has been developed. This new protocol provides a facile approach for the asymmetric synthesis of benzothiazolo-pyrimidinones and a pyrrolo[1,2-a] indolone in moder...

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Published inChemical communications (Cambridge, England) Vol. 51; no. 7; pp. 1263 - 1266
Main Authors Ni, Qijian, Song, Xiaoxiao, Xiong, Jiawen, Raabe, Gerhard, Enders, Dieter
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.01.2015
Subjects
Catalysis
Chemistry
Chemistry, Multidisciplinary
Imines - chemistry
Lactams - chemistry
Methane - analogs & derivatives
Methane - chemistry
Models, Molecular
Molecular Conformation
Physical Sciences
Pyrimidinones - chemistry
Science & Technology
Stereoisomerism
Substrate Specificity
Thiazoles - chemistry
HIGHLY ENANTIOSELECTIVE SYNTHESIS
MESOIONIC XANTHINE ANALOGS
DIELS-ALDER REACTIONS
SPIRO-HETEROCYCLES
ONE-POT SYNTHESIS
N-HETEROCYCLIC-CARBENE
CONJUGATE UMPOLUNG
GAMMA-BUTYROLACTONES
BETA-LACTAMS
ANNULATION REACTIONS
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Summary:An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with alpha-chloroaldehydes has been developed. This new protocol provides a facile approach for the asymmetric synthesis of benzothiazolo-pyrimidinones and a pyrrolo[1,2-a] indolone in moderate to good yields (34-78%) and excellent stereoselectivities (87-99% ee, up to > 20 : 1 d.r.).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc08594a