A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: a formal synthesis of (S)-coniine from L-norvaline

作者：Karanfil Abdullah; Balta Berrin; Eskici Mustafa^*

来源：Tetrahedron, 2012, 68(49): 10218-10229.

DOI：10.1016/j.tet.2012.09.081

• Cyclic sulfamidates
• Lithium triethylorthopropiolate
• Cyclization
• Piperidines

Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding delta-amino-alpha,beta-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from L-norvaline.

• 出版日期2012-12-9