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분자활성 촉매반응 연구단
분자활성 촉매반응 연구단
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Dynamic Kinetic Resolution of Alkenyl Cyanohydrins Derived from α,β-Unsaturated Aldehydes: Stereoselective Synthesis of E-Tetrasubstituted Olefins

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Title
Dynamic Kinetic Resolution of Alkenyl Cyanohydrins Derived from α,β-Unsaturated Aldehydes: Stereoselective Synthesis of E-Tetrasubstituted Olefins
Author(s)
Jadab Majh; Ben W. H. Turnbull; Ho Ryu; Jiyong Park; Mu-Hyun Baik; P. Andrew Evans
Publication Date
2019-07
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.30, pp.11770 - 11774
Publisher
AMER CHEMICAL SOC
Abstract
© 2019 American Chemical Society.A novel dynamic kinetic resolution (DKR) of tetrasubstituted alkenyl cyanohydrins prepared from the corresponding α,β-unsaturated aldehydes is described. The deprotonation of a geometrical mixture of tetrasubstituted alkenyl cyanohydrins with sodium diisopropylamide (NaDA) affords the allylic anions, which enables the equilibration of the E- and Z-olefins to permit the selective functionalization of the E-adduct. Theoretical studies indicate that the nature of the alkali metal cation is a critical component to lowering the barrier for interconversion between the two geometrical isomers, which provides the mechanistic basis for the DKR reaction. In addition, we demonstrate that the DKR reaction can be combined with a transition metal-catalyzed allylic substitution to generate a stereodefined E-tetrasubstituted olefin and quaternary center in a single cross-coupling reaction
URI
https://pr.ibs.re.kr/handle/8788114/6459
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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