Nickel-catalyzed regio- and enantioselective aminolysis of 3,4-epoxy alcohols

Journal of the American Chemical Society
Chuan Wang, Hisashi Yamamoto

Abstract

The first catalytic regio- and enantioselective aminolysis of 3,4-epoxy alcohols has been accomplished. Under the catalysis of Ni(ClO4)2·6H2O, the C4 selective ring opening of various 3,4-epoxy alcohols proceeded in a stereospecific manner with high regioselectivities. Furthermore, with the Ni-BINAM catalytic system the enantioselective ring opening of 3,4-epoxy alcohols furnished various γ-hydroxy-δ-amino alcohols as products with complete regiocontrol and high enantioselectivities (up to 94% ee).

References

Jan 11, 2007·Journal of the American Chemical Society·Wei Zhang, Hisashi Yamamoto
May 21, 2010·Journal of the American Chemical Society·Zhi Li, Hisashi Yamamoto
Feb 15, 2013·Journal of the American Chemical Society·José Luis Olivares-RomeroHisashi Yamamoto
Jan 16, 2014·Journal of the American Chemical Society·Chuan Wang, Hisashi Yamamoto
Apr 30, 2014·Journal of the American Chemical Society·Chuan Wang, Hisashi Yamamoto

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Citations

Jan 21, 2016·Accounts of Chemical Research·Chuan WangHisashi Yamamoto
Nov 3, 2016·Journal of the American Chemical Society·Hiroaki Tsuji, Hisashi Yamamoto
Jan 5, 2017·Chemical & Pharmaceutical Bulletin·Shun-Ichiro UesugiYoshiharu Iwabuchi
Sep 28, 2018·Organic & Biomolecular Chemistry·Hongqing YaoChuan Wang
Mar 23, 2019·Organic & Biomolecular Chemistry·Daichi NakamuraYoshiharu Iwabuchi
Nov 15, 2017·Organic & Biomolecular Chemistry·Suguru ItoMasatoshi Asami
Mar 19, 2019·Chemical Science·Amit Banerjee, Hisashi Yamamoto
Nov 17, 2020·Chemistry : a European Journal·Yuse KuriyamaYoshiharu Iwabuchi
Feb 28, 2018·The Journal of Organic Chemistry·Takahiro Sawano, Hisashi Yamamoto
Oct 21, 2020·The Journal of Organic Chemistry·Aran K Hubbell, Geoffrey W Coates
Aug 28, 2018·Organic Letters·Grace WangMark S Taylor
Mar 24, 2018·Chemical Reviews·Sukalyan Bhadra, Hisashi Yamamoto

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