2018ChiralityRequires access

Highly enantioselective Michael addition of α‐nitroacetate to α,β‐unsaturated pyrazolamide catalyzed by a bifunctional squaramide

Ying‐Ying Liu, Ling Ye, Zhichuan Shi, Xuejun Yang, Zhigang Zhao, Xuefeng Li

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Abstract

A highly enantioselective (91- > 99% ee) Michael addition of α-nitroacetate to α,β-unsaturated pyrazolamide was developed in the presence of a bifunctional squaramide. Satisfactory isolated yields (42%-99%) have been achieved with a wide range of α,β-unsaturated pyrazolamides, albeit acceptor of this type displayed poor reactivity in the precedent reports. The adducts resulting from this protocol are useful synthetic intermediates for further synthetic modification.

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What this paper is about

A highly enantioselective (91- > 99% ee) Michael addition of α-nitroacetate to α,β-unsaturated pyrazolamide was developed in the presence of a bifunctional squaramide. Satisfactory isolated yields (42%-99%) have been achieved with a wide range of α,β-unsaturated pyrazolamides, albeit acceptor of this type displayed poor reactivity in the precedent reports. The adducts resulting from this protocol are useful synthetic intermediates for further synthetic modification.

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Available abstract

A highly enantioselective (91- > 99% ee) Michael addition of α-nitroacetate to α,β-unsaturated pyrazolamide was developed in the presence of a bifunctional squaramide. Satisfactory isolated yields (42%-99%) have been achieved with a wide range of α,β-unsaturated pyrazolamides, albeit acceptor of this type displayed poor reactivity in the precedent reports. The adducts resulting from this protocol are useful synthetic intermediates for further synthetic modification.

Key concepts: Squaramide, Enantioselective synthesis, Bifunctional, Chemistry, Michael reaction, Reactivity (psychology), Adduct, Catalysis

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