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

ABSTRACT: An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with ?-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.).

SUBMITTER: Ni Q 

PROVIDER: S-EPMC4612130 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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

Ni Qijian Q   Song Xiaoxiao X   Xiong Jiawen J   Raabe Gerhard G   Enders Dieter D  

Chemical communications (Cambridge, England) 20150101 7

An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with α-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.). ...[more]

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