Asymmetric Redox-Annulation of Cyclic Amines

The Journal of Organic Chemistry
YoungKu KangDaniel Seidel

Abstract

Cyclic amines such as 1,2,3,4-tetrahydroisoquinoline undergo regiodivergent annulation reactions with 4-nitrobutyraldehydes. These redox-neutral transformations enable the asymmetric synthesis of highly substituted polycyclic ring systems in just two steps from commercial materials. The utility of this process is illustrated in a rapid synthesis of (-)-protoemetinol. Computational studies provide mechanistic insights and implicate the elimination of acetic acid from an ammonium nitronate intermediate as the rate-determining step.

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Citations

Feb 20, 2016·Organic Letters·Weijie Chen, Daniel Seidel
Jan 20, 2016·Organic Letters·Zhengbo Zhu, Daniel Seidel
Aug 12, 2016·Organic Letters·YoungKu Kang, Daniel Seidel
Jul 25, 2017·Organic & Biomolecular Chemistry·Jianjun LiWei Wang
Jan 16, 2018·Organic & Biomolecular Chemistry·Wannaporn Disadee, Somsak Ruchirawat
Jun 26, 2018·Organic Letters·Zhengbo ZhuDaniel Seidel
May 17, 2017·Organic Letters·Zhengbo Zhu, Daniel Seidel
Nov 17, 2017·Organic Letters·Zhengbo ZhuDaniel Seidel
Mar 7, 2019·Organic Letters·Anirudra PaulDaniel Seidel
Jan 28, 2020·Organic Letters·Anirudra PaulDaniel Seidel
Jan 13, 2018·Organic Letters·Anirudra PaulDaniel Seidel

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Methods Mentioned

BETA
column chromatography
nuclear magnetic resonance
NMR

Software Mentioned

MacroModel
Gaussian

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