Direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates.

Angewandte Chemie
Raquel de la CampaDarren J Dixon

Abstract

A catalytic asymmetric aldol addition/cyclization reaction of unactivated ketones with isocyanoacetate pronucleophiles has been developed. A quinine-derived aminophosphine precatalyst and silver oxide were found to be an effective binary catalyst system and promoted the reaction to afford chiral oxazolines possessing a fully substituted stereocenter with good diastereoselectivities and excellent enantioselectivities.

References

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Citations

Oct 30, 2015·Organic & Biomolecular Chemistry·Allegra FranchinoDarren J Dixon
Nov 10, 2015·Chemistry : a European Journal·Pier Giorgio CozziJanusz Lewinski
Aug 9, 2016·Chemical Communications : Chem Comm·Raquel de la CampaDarren J Dixon
May 31, 2018·Chemical Society Reviews·Yasuhiro YamashitaShū Kobayashi
Sep 25, 2018·Chemistry : a European Journal·Allegra FranchinoDarren J Dixon
Jul 22, 2018·Nature Communications·Lan-Gui Xie, Darren J Dixon
Feb 25, 2021·Organic & Biomolecular Chemistry·Linqing WangDongxu Yang
Sep 18, 2018·Organic Letters·Raquel de la CampaDarren J Dixon
Dec 13, 2018·The Journal of Organic Chemistry·Pablo Martínez-PardoJosé R Pedro
Jan 27, 2019·Organic Letters·Xu-Cheng Gan, Liang Yin
Dec 15, 2016·Chemical Reviews·Hélène Pellissier
Dec 25, 2019·The Journal of Organic Chemistry·Gerard P RobertsonDarren J Dixon

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Methods Mentioned

BETA
column chromatography
X-ray

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