A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine

Yang Yang,Dean P Phillips,Shifeng Pan

doi:10.1016/j.tetlet.2011.01.090

A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine

Yang Yang, Dean P Phillips + Show 1 more

https://doi.org/10.1016/j.tetlet.2011.01.090

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Journal: Tetrahedron Letters	Publication Date: Jan 31, 2011
Citations: 22

Affiliation: Genomics Institute of the Novartis Research Foundation

#Vinylogous Mannich Reactions #Silyl Ketene Acetal + Show 8 more

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Abstract

A three-component diastereoselective vinylogous Mannich-type reaction (VMR) with the silyl ketene acetal (1) was developed. Adducts from the reactions provided valuable intermediates for construction of a variety of chiral 6-alkylated piperidinone and 2-piperidine compounds. The strategy was applied in a concise synthesis (S)-anabasine.

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