Exploiting β-Amino Acid Enolates in Direct Catalytic Diastereo- and Enantioselective C-C Bond-Forming Reactions

Chemistry : a European Journal
Jin-Sheng YuMasakatsu Shibasaki

Abstract

In contrast to the widespread use of α-amino acid-equivalent enolates for the preparation of non-natural amino acids, the utilization of β-amino-acid counterparts has been limited. This deficit has resulted in a short supply of β2, 2 -amino acids bearing two substituents at the α-carbon, especially for peptide synthesis. Herein, racemic 4-substituted isoxazolidin-5-ones were used as precursors of β2 -amino acid enolates in the direct catalytic diastereo- and enantioselective C-C bond-forming reactions, constructing two adjacent stereocenters in a highly stereoselective fashion. The obtained adducts were smoothly coupled with α-amino acid-derived α-ketoacids to afford α/β2, 2 -hybrid dipeptides suitable for 9-fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. Moreover, the Mannich adducts obtained from isatin-derived imines were converted to spirocyclic β-lactams, which have recently received increased attention due to their unique biological activities and conformational preferences.

References

Jun 13, 2002·Chemical Reviews·Masakatsu Shibasaki, Naoki Yoshikawa
Feb 15, 2003·The Journal of Organic Chemistry·Hee-Seung LeeSamuel H Gellman
Dec 12, 2003·Journal of Medicinal Chemistry·Roger M Freidinger
Aug 31, 2007·Organic & Biomolecular Chemistry·Marie-Isabel AguilarPatrick Perlmutter
Oct 6, 2007·Chemical Reviews·Carmen Najera, José M Sansano
Aug 2, 2008·European Journal of Medicinal Chemistry·Girija S Singh, Patrick Luntha
May 14, 2009·Accounts of Chemical Research·Masakatsu ShibasakiNaoya Kumagai
Jun 17, 2002·Angewandte Chemie·William S Knowles
Apr 27, 2010·Chemical Society Reviews·Barbara WeinerBen L Feringa
Apr 5, 2011·Amino Acids·Ludwig K A Pilsl, Oliver Reiser
Jul 14, 2011·Chembiochem : a European Journal of Chemical Biology·Rob M J LiskampJohan Kemmink
Oct 16, 2012·Chemistry : a European Journal·Lara MataJesús M Peregrina
Nov 30, 2012·Angewandte Chemie·Katrien Brak, Eric N Jacobsen
Jun 12, 2013·Organic & Biomolecular Chemistry·Sun Min Kim, Jung Woon Yang
Nov 2, 2013·Chemical Communications : Chem Comm·Tony TiteJean-François Brière
Apr 25, 2014·Current Topics in Medicinal Chemistry·Fernando RodriguezMaria Del Mar Zurbano
Sep 11, 2014·Journal of Medicinal Chemistry·Chiara CabreleLukasz Berlicki
Nov 22, 2014·Chemistry : a European Journal·Iván García-GonzálezJesús M Peregrina
Dec 17, 2014·The Journal of Organic Chemistry·Alison E Metz, Marisa C Kozlowski
Jul 3, 2015·Current Opinion in Chemical Biology·Halina M Werner, W Seth Horne
Oct 13, 2015·Journal of Medicinal Chemistry·Bradley C DoakJan Kihlberg
Jan 15, 2016·Bioorganic & Medicinal Chemistry Letters·Paulina Wójcik, Łukasz Berlicki
Apr 7, 2016·Nature Reviews. Drug Discovery·Duncan E ScottJohn Skidmore
Sep 15, 2016·Chemistry : a European Journal·Timothée CadartJean-François Brière
Sep 20, 2017·Journal of Medicinal Chemistry·David A DeGoeyMichael D Wendt
Oct 3, 2017·Journal of Medicinal Chemistry·Loes M SteversChristian Ottmann
Feb 13, 2018·Chemistry : a European Journal·Marllon Nascimento de OliveiraJanine Cossy
Apr 18, 2018·Organic & Biomolecular Chemistry·Jasneet Kaur, Swapandeep Singh Chimni

❮ Previous
Next ❯

Citations

Jul 26, 2019·Chemical & Pharmaceutical Bulletin·Fuyuki AmemiyaMasakatsu Shibasaki
Dec 13, 2019·Chemical Communications : Chem Comm·Andreas EitzingerMario Waser
Jan 10, 2020·Organic & Biomolecular Chemistry·Andreas EitzingerMario Waser
Mar 20, 2020·Organic & Biomolecular Chemistry·Suo-Suo QiDan-Qian Xu
Jun 10, 2020·Organic & Biomolecular Chemistry·Jasneet KaurSwapandeep Singh Chimni
Dec 7, 2018·Organic Chemistry Frontiers : an International Journal of Organic Chemistry·Vito CapaccioMario Waser
Nov 7, 2019·Chemical & Pharmaceutical Bulletin·Hidetoshi Noda, Masakatsu Shibasaki
Jun 13, 2019·Journal of the American Chemical Society·Jin-Sheng YuMasakatsu Shibasaki
Dec 3, 2021·Chemical & Pharmaceutical Bulletin·Hidetoshi Noda
Jan 12, 2022·Organic & Biomolecular Chemistry·Victoria HaiderMario Waser

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.