Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates

Yoshida, Masanori; Masaki, Erika; Ikehara, Hiroto; Hara, Shoji

Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates

Yoshida, Masanori; Masaki, Erika; Ikehara, Hiroto et al.

Organic & Biomolecular Chemistry, 2012, 10(27), 5289-5297

Permalink : https://hdl.handle.net/2115/52715

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アクセス権	open access
URI	https://hdl.handle.net/2115/52715
タイトル	Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates
著者	Yoshida, Masanori ; Masaki, Erika ; Ikehara, Hiroto ; Hara, Shoji
e-Rad_Researcher 30322829 著者名 Yoshida, Masanori
著者名 Masaki, Erika
著者名 Ikehara, Hiroto
e-Rad_Researcher 20109490 著者名 Hara, Shoji
言語	英語
発行日	2012-07-21
出版者	Royal Society of Chemistry
収録物名	Organic & Biomolecular Chemistry
巻(号)	10(27)
ページ	5289-5297
抄録	Michael addition reaction of α-branched aldehydes to β-nitroacrylates was successfully carried out by using a mixed catalyst consisting of a primary amino acid, L-phenylalanine, and its lithium salt to give β-formyl-β'-nitroesters having a quaternary carbon centre in good yields (up to 85%) with high enantioselectivity (up to 98% ee). By using benzyl β-nitroacrylates as Michael acceptors, the obtained β-formyl-β'-nitroesters were converted into various 4,4-disubstituted pyrrolidine-3-carboxylic acids including analogues of gabapentin (Neurotin®) in one step from the Michael adducts in high yields.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	Org. Biomol. Chem., 2012,10, 5289-5297 - Reproduced by permission of The Royal Society of Chemistry (RSC)
PISSN	1477-0520
関連情報	PMID 22678163
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1039/c2ob25413a