Enantioselective synthesis of polycyclic nitrogen heterocycles by Rh-catalyzed alkene hydroacylation: constructing six-membered rings in the absence of chelation assistance

Organic Letters
Xiang-Wei DuLevi M Stanley

Abstract

Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities.

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Citations

Sep 24, 2015·Organic Letters·Kirsten F JohnsonLevi M Stanley
Jun 2, 2017·Journal of the American Chemical Society·Yujing ZhouStephen L Buchwald
May 21, 2016·Organic & Biomolecular Chemistry·James D Neuhaus, Michael C Willis
Mar 12, 2016·Organic & Biomolecular Chemistry·Sudam Ganpat DawandeSreenivas Katukojvala
Oct 26, 2016·Organic & Biomolecular Chemistry·James A Walker, Levi M Stanley
Mar 16, 2017·Journal of Physics. Condensed Matter : an Institute of Physics Journal·L D Contreras-Pulido, M Bruderer
Oct 21, 2016·Chemistry : a European Journal·Kirsten F JohnsonLevi M Stanley
Nov 4, 2016·Organic & Biomolecular Chemistry·Wen-Wen Chen, Ming-Hua Xu
Nov 30, 2019·Chemical Communications : Chem Comm·Shao-Chi LeeMagnus Rueping
Jul 8, 2021·Chemical Communications : Chem Comm·Yang Yang, Dong Xing
Dec 5, 2017·Organic Letters·Kolluru Srinivas, Chepuri V Ramana
Dec 23, 2020·Journal of Chemical Information and Modeling·Rafael MamedeJoao Aires-de-Sousa
Aug 14, 2020·The Journal of Organic Chemistry·Rodrigo A CormanichFernando Coelho

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Methods Mentioned

BETA
hydroacylation
hydroacylations
X-ray
NMR

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