Stereodivergent Synthesis of Enantioenriched 2-Pyrrolidones via Diastereoselective Hydrogenation of α,β-Unsaturated γ-Lactams

Guo，Siyuan1; Ma，Baode1; Chen，Gen Qiang2; Zhang，Xumu1

2023

10.1021/acs.orglett.3c00532

Organic Letters   Impact Factor & Quartile

1523-7060

1523-7052

Synthesis of optically enriched racetam analogues was achieved via highly remote diastereocontrolled and enantiocontrolled Pd/C-catalyzed hydrogenation of α,β-unsaturated γ-lactams. Various mono- and disubstituted 2-pyrrolidones were obtained in excellent yields and stereoselectivities, and a concise and large-scale synthesis of brivaracetam was developed from inexpensive l-2-aminobutyric acid. Surprisingly, stereodivergent hydrogenation was observed by modifying remote functionalized stereocenters and additives, which would provide alternative stereochemical options of chiral racetams synthesis.

SCI

English

NI Journal Papers

First ; Corresponding

National Key R&D Program of China[2021YFA1500201] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17213101] ; Stable Support Plan Program of Shenzhen Natural Science Fund[20200925161222002] ; Key-Area Research and Development Program of Guangdong Province[2020B010188001] ; Innovative Team of Universities in Guangdong Province[2020KCXTD016] ; National Natural Science Foundation of China["21991113","21901107"] ; Shenzhen Science and Technology Innovation Committee[22171129] ; null[JCYJ20210324104202007]

Chemistry

Chemistry, Organic

WOS:000966979400001

AMER CHEMICAL SOC

CHEMISTRY

2-s2.0-85151836474

Scopus

1.Medi-X Pingshan and Department of Chemistry,Southern University of Science and Technology,Shenzhen,518000,China
2.Academy for Advanced Interdisciplinary Studies and Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China

Guo，Siyuan,Ma，Baode,Chen，Gen Qiang,et al. Stereodivergent Synthesis of Enantioenriched 2-Pyrrolidones via Diastereoselective Hydrogenation of α,β-Unsaturated γ-Lactams[J]. Organic Letters,2023.

Guo，Siyuan,Ma，Baode,Chen，Gen Qiang,&Zhang，Xumu.(2023).Stereodivergent Synthesis of Enantioenriched 2-Pyrrolidones via Diastereoselective Hydrogenation of α,β-Unsaturated γ-Lactams.Organic Letters.

Guo，Siyuan,et al."Stereodivergent Synthesis of Enantioenriched 2-Pyrrolidones via Diastereoselective Hydrogenation of α,β-Unsaturated γ-Lactams".Organic Letters (2023).