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Cu-I-Catalysed Enantioselective Alkyl 1,4-Additions to (E)-Nitroalkenes and Cyclic Enones with Phosphino-Oxazoline Ligands
- Cu-I-Catalysed Enantioselective Alkyl 1,4-Additions to (E)-Nitroalkenes and Cyclic Enones with Phosphino-Oxazoline Ligands
- Shin, Minkyeong; Gu, Minji; Lim, Sung Soo; Kim, Min-Jae; Lee, JuHyung; Jin, HyeongGyu; Jang, Yun Hee; Jung, Byung Hyuck
- DGIST Authors
- Jang, Yun Hee; Jung, Byung Hyuck
- Issue Date
- European Journal of Organic Chemistry(24), 3122-3130
- Article Type
- Author Keywords
- Asymmetric catalysis; Michael addition; Nucleophilic addition; N; P ligands; Ligand design; Zinc
- ASYMMETRIC CONJUGATE ADDITION; ALLYLIC SUBSTITUTION-REACTIONS; ORGANOMETALLIC REAGENTS; DIALKYLZINC REAGENTS; STEREOGENIC CENTERS; TERTIARY ALCOHOLS; MICHAEL ADDITIONS; NITROALKENES; EFFICIENT; HYDROGENATION
- 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
- John Wiley & Sons Ltd.
- Related Researcher
Organic Synthesis; Organo-transition metal chemistry
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