Atom-Economic Synthesis of Pentaleno[2,1-b]indoles via Tandem Cyclization of Alkynones Initiated by Aminopalladation

作者：Chen, Junjie; Han, Xiuling^*; Lu, Xiyan^*

来源：Journal of Organic Chemistry, 2017, 82(4): 1977-1985.

DOI：10.1021/acs.joc.6b02817

• NONREARRANGED MONOTERPENOID UNIT
• SIMPLE INDOLE ALKALOIDS
• CASCADE CYCLIZATION
• EFFICIENT SYNTHESIS
• CATALYZED REACTIONS
• DOMINO REACTIONS
• CARBON-CARBON
• ALKYNES
• BONDS
• FUNCTIONALIZATION

An atom-economic Pd(OAc)(2)-catalyzed tandem cyclization of alkynones to synthesize pentaleno[2,1-b]indoles was developed efficiently. In the formed tetracyclic indole framework, two neighboring stereocenters, one being all-carbon quaternary, are being constructed in a single process with excellent diastereoselectivity. This reaction was initiated by aminopalladation of alkynes and quenched by addition to the intramolecular carbonyl groups.

• 出版日期2017-2-17
• 单位金属有机化学国家重点实验室; 中国科学院