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Cu-I-Catalysed Enantioselective Alkyl 1,4-Additions to (E)-Nitroalkenes and Cyclic Enones with Phosphino-Oxazoline Ligands

Title
Cu-I-Catalysed Enantioselective Alkyl 1,4-Additions to (E)-Nitroalkenes and Cyclic Enones with Phosphino-Oxazoline Ligands
Authors
Shin, MinkyeongGu, MinjiLim, Sung SooKim, Min-JaeLee, JuHyungJin, HyeongGyuJang, Yun HeeJung, Byung Hyuck
DGIST Authors
Jang, Yun HeeJung, Byung Hyuck
Issue Date
2018-06
Citation
European Journal of Organic Chemistry(24), 3122-3130
Type
Article
Article Type
Article
Author Keywords
Asymmetric catalysisMichael additionNucleophilic additionNP ligandsLigand designZinc
Keywords
ASYMMETRIC CONJUGATE ADDITIONALLYLIC SUBSTITUTION-REACTIONSORGANOMETALLIC REAGENTSDIALKYLZINC REAGENTSSTEREOGENIC CENTERSTERTIARY ALCOHOLSMICHAEL ADDITIONSNITROALKENESEFFICIENTHYDROGENATION
ISSN
1434-193X
Abstract
Catalytic enantioselective conjugate additions of simple alkyl groups to nitroalkenes or cyclic enones that result in the formation of tertiary C–C bonds are described. For these stereoselective addition reactions, new chiral phosphino-oxazoline ligands were synthesized and used. The reactions were promoted by a Cu-based catalyst (2 mol-%), and gave the chiral products in up to 92 % yield with 95 % ee. A larger-scale synthesis was demonstrated, and the origin of the stereoselectivity was proposed based on DFT calculations. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
http://hdl.handle.net/20.500.11750/9009
DOI
10.1002/ejoc.201800476
Publisher
John Wiley & Sons Ltd.
Related Researcher
  • Author Jung, Byunghyuck  
  • Research Interests Organic Synthesis; Organo-transition metal chemistry
Files:
There are no files associated with this item.
Collection:
Department of Energy Science and EngineeringCMMM Lab(Curious Minds Molecular Modeling Laboratory)1. Journal Articles
School of Undergraduate Studies1. Journal Articles


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