Highly enantioselective synthesis of chiral allenes by sequential creation of stereogenic center and chirality transfer in a single pot operation

Organic Letters
Mariappan PeriasamyPolimera Obula Reddy

Abstract

Chiral allenes are readily accessed in a single pot operation in the reaction of terminal alkynes, aldehydes, chiral secondary amines, and zinc halides in good yields (up to 77% yield) and excellent enantioselectivities (up to 99% ee) in toluene at 120 °C. The reaction proceeds through initial formation of chiral propargylamine intermediates with creation of a new stereogenic center and subsequent chirality transfer via an intramolecular hydride shift to produce chiral allenes with high enantiomeric purities.

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Citations

Jun 19, 2013·Chemical Reviews·Annette D Allen, Thomas T Tidwell
Nov 6, 2015·Journal of the American Chemical Society·Qi-Kai KangYong Tang
Apr 24, 2016·Chemistry : a European Journal·Manjeet K MajhailMichael C Willis
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Mar 6, 2015·Organic & Biomolecular Chemistry·Jiasheng ZhangShengming Ma
Aug 22, 2013·Chemical Communications : Chem Comm·Xinjun TangShengming Ma
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Nov 13, 2012·Chemistry : a European Journal·Juntao YeShengming Ma
Mar 31, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jia-Nan MoJiannan Zhao
Apr 8, 2014·Angewandte Chemie·Michael C Haibach, Daniel Seidel
Mar 31, 2021·Organic Letters·Jun Li, Scott R Gilbertson
Mar 16, 2013·Journal of the American Chemical Society·Ian T CrouchDoug E Frantz
Apr 16, 2019·Accounts of Chemical Research·Xin Huang, Shengming Ma
Nov 26, 2013·The Journal of Organic Chemistry·Guo-Jie JiangZhi-Xiang Yu
Apr 24, 2013·Organic Letters·Ruizhi LüShengming Ma
Mar 11, 2015·The Journal of Organic Chemistry·Mariappan PeriasamyPolimera Obula Reddy
Apr 4, 2015·Journal of the American Chemical Society·Chenfei Zhao, Daniel Seidel
Sep 23, 2021·ACS Omega·Leandros P ZorbaGeorgios C Vougioukalakis

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