Asymmetric Synthesis of Adamantyl GABA Analogues

Anastasiya E. Sibiryakova; Vadim A. Shiryaev; Alexander N. Reznikov; Anastasiya A. Kabanova; Yuri N. Klimochkin

doi:10.1055/s-0037-1610824

Synthesis, Table of Contents

Synthesis 2019; 51(02): 463-469
DOI: 10.1055/s-0037-1610824

paper

Asymmetric Synthesis of Adamantyl GABA Analogues

Anastasiya E. Sibiryakova*

Department of Organic Chemistry, Samara State Technical University, Samara 443100, Molodogvardeyskaya st. 244, Russian Federation Email: hom92_92@mail.ru Email: shirv@mail.ru

,

Vadim A. Shiryaev*

Department of Organic Chemistry, Samara State Technical University, Samara 443100, Molodogvardeyskaya st. 244, Russian Federation Email: hom92_92@mail.ru Email: shirv@mail.ru

,

Alexander N. Reznikov

,

Anastasiya A. Kabanova

,

Yuri N. Klimochkin

› Author Affiliations

Abstract

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Abstract

An efficient synthesis of (R)- and (S)-4-amino-3-(adamant-1-yl)butyric acids and (R)- and (S)-4-(adamant-1-yl)pyrrolidin-2-ones is presented. The synthetic strategy is based on asymmetric Michael addition of diethyl malonate to 1-(adamant-1-yl)-2-nitroethene using available Ni(II) complex as the catalyst. The procedures provide good to high enantioselectivity of Michael addition to sterically hindered nitroalkene and good yields of (R)- and (S)-enantiomers of 3-adamantyl substituted GABA.

Key words

Michael reaction - asymmetric synthesis - metal complex catalysis - chiral GABA analogues - optical rotation calculations

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References

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