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Replication of α-amino acids via Strecker synthesis with amplification and multiplication of chiral intermediate aminonitriles

Autor: Tsuneomi Kawasaki, Shohei Aiba, Naoya Takamatsu, Yuji Tokunaga, Taichiro Sasai

Publikováno v: Chemical Communications. 52:10834-10837

Replication of chiral l- and d-α-(p-tolyl)glycine has been achieved in combination with the asymmetric induction, amplification and multiplication of their own chiral intermediates, l- and d-aminonitriles, in the solid-phase via the Strecker reactio

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::38cba4886a5bfc75ee1c4ac846a4b620
https://doi.org/10.1039/c6cc05544c

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Studies toward the enantioselective synthesis of neurymenolide A: Construction of the macrocyclic core via Claisen rearrangement

Autor: Shohei Aiba, Tetsuji Murase, Natsuki Sakurai, Masahiro Masuda, Yusuke Ogura, Naoki Mori, Hidenori Watanabe, Tsuneomi Kawasaki, Hirosato Takikawa

Publikováno v: Tetrahedron Letters. 61:151825

Neurymenolides, α-pyrone macrolides isolated from the Fijian red alga Neurymenia fraxinifolia, are anti-methicillin-resistant Staphylococcus aureus and anti-vancomycin-resistant Enterococcus faecium compounds. In this study, the macrocyclic core of

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::9401bf0371014224844ddba6e615b1ce
https://doi.org/10.1016/j.tetlet.2020.151825

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Synthesis of anti-Helicobacter pylori sesquiterpene employing tandem radical cyclization, and determination of the absolute configuration of the natural product

Autor: Shohei Aiba, Shinya Yamada, Hirosato Takikawa, Tsuneomi Kawasaki, Ken Ishigami, Arata Yajima, Ryo Katsuta, Kazuki Kadowaki, Tomoo Nukada, Hidenori Watanabe

Publikováno v: Tetrahedron. 76:130834

Both enantiomers of (Z)-2β-hydroxy-14-hydro-β-santalol, a potent anti-H. pylori agent, were synthesized and the absolute configuration of the natural product was determined to be 1R,2S,3R,4S. The bicyclo[2.2.1]heptane skeleton was efficiently const

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::553ed291dbf2498bb5f41adc2d287e16
https://doi.org/10.1016/j.tet.2019.130834

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Highly Stereoselective Strecker Synthesis Induced by a Slight Modification of Benzhydrylamine from Achiral to Chiral

Autor: Shohei Aiba, Yuji Tokunaga, Tsuneomi Kawasaki, Takuya Yamada, Naoya Takamatsu

Publikováno v: Chemistry (Weinheim an der Bergstrasse, Germany). 24(6)

2-Methylbenzhydrylamine is a chiral variant of achiral benzhydrylamine; however, the chirality formed from the small difference between the phenyl and o-tolyl groups is not expected to induce sufficient stereoselectivity in conventional homogeneous r

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d3aa11b1cd837e2e9b145a0a3da97910
https://pubmed.ncbi.nlm.nih.gov/28980348

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Asymmetric Strecker Reaction Arising from the Molecular Orientation of an Achiral Imine at the Single-Crystal Face: Enantioenriched l- and d-Amino Acids

Autor: Naoya Takamatsu, Yusuke Yamazaki, Shinobu Miyagawa, Koji Yoshimura, Shohei Aiba, Tsuneomi Kawasaki, Tetsuya Kuraishi, Yuji Tokunaga

Publikováno v: Angewandte Chemie (International ed. in English). 56(4)

Strecker synthesis has long been considered one of the prebiotic reactions for the synthesis of α-amino acids. However, the correlation between the origin of chirality and highly enantioenriched α-amino acids through this method remains a puzzle. I

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9027b313b726bc08279ad0637d6369e5
https://pubmed.ncbi.nlm.nih.gov/28004489

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ChemInform Abstract: Spontaneous Formation and Amplification of an Enantioenriched α-Amino Nitrile: A Chiral Precursor for Strecker Amino Acid Synthesis

Autor: Naoya Takamatsu, Tsuneomi Kawasaki, Yuji Tokunaga, Shohei Aiba

Publikováno v: ChemInform. 46

Without the addition of any chiral substances, the spontaneous formation of an enantioenriched α-amino nitrile (up to 96% ee), which is a chiral precursor for Strecker amino acid synthesis, is achieved in combination with conglomerate formation.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::7dbf1d5a086985ab5c5eaa0a9aad383e
https://doi.org/10.1002/chin.201544029

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Spontaneous formation and amplification of an enantioenriched α-amino nitrile: a chiral precursor for Strecker amino acid synthesis

Autor: Naoya Takamatsu, Yuji Tokunaga, Shohei Aiba, Tsuneomi Kawasaki

Publikováno v: Chemical communications (Cambridge, England). 51(76)

Without the addition of any chiral substances, the spontaneous formation of an enantioenriched α-amino nitrile (up to 96% ee), which is a chiral precursor for Strecker amino acid synthesis, has been achieved in combination with conglomerate formatio

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7121c7b719affccf76b300a81bfb27fe
https://pubmed.ncbi.nlm.nih.gov/26269321

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