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Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with ?-Chloro Aldehydes.

ABSTRACT: Diastereo- and enantioselective N-heterocyclic carbene catalyzed 1-azadiene Diels-Alder reactions of (E)-2-styrylbenzothiazoles with ?-chloro aldehydes are reported. This annulation strategy provides an efficient access to medicinally important dihydrobenzothiazolopyridin-1-ones in good to excellent yields (44-97%) with very good to excellent stereoselectivities (up to 9:1 dr, 98% ee) and tolerates quite a range of substituents.

SUBMITTER: Song X 

PROVIDER: S-EPMC4702348 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes.

Song Xiaoxiao X   Ni Qijian Q   Zhu Chen C   Raabe Gerhard G   Enders Dieter D  

Synthesis 20141101 3

Diastereo- and enantioselective N-heterocyclic carbene catalyzed 1-azadiene Diels-Alder reactions of (<i>E</i>)-2-styrylbenzothiazoles with α-chloro aldehydes are reported. This annulation strategy provides an efficient access to medicinally important dihydrobenzothiazolopyridin-1-ones in good to excellent yields (44-97%) with very good to excellent stereoselectivities (up to 9:1 dr, 98% ee) and tolerates quite a range of substituents. ...[more]

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