A new entry into 3-hydroxypyrrolidine derivatives from protected α- or β-amino esters
نویسندگان
چکیده
منابع مشابه
One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters
An improved protocol for the synthesis of enantiomerically pure allylic amines is reported. N-Protected α-amino esters derived from natural amino acids were submitted to a one-pot tandem reduction-olefination process. The sequential reduction with DIBAL-H at -78 °C and subsequent in situ addition of organophosphorus reagents yielded the corresponding allylic amines without the need to isolate t...
متن کاملDivergent, stereoselective access to heterocyclic α,α-quaternary- and β(2,3,3)-amino acid derivatives from a N-Pmp-protected Orn-derived β-lactam.
A suitably protected Orn-derived (3S,4S)-β-lactam was used as common intermediate in the synthesis of conformationally constrained (3S,4S)-2-oxoazepane α,α- and (2S,3S)-2-oxopiperidine-β(2,3,3)-amino acid derivatives. Compared to alternative procedures using an N-p-methoxybenzyl group at the 2-azetidinone, the incorporation of a p-methoxyphenyl moiety is crucial for the excellent stereochemical...
متن کاملThe Solvent Free Preparation of β-Amino Esters α,β-Unsaturated Ketones and Esters with Domestic Microwave Oven
Uma série de cetonas e ésteres α,β-insaturados β-amino ésteres, 4a-h e 6a-d, derivados de α-amino ácidos foi obtida a partir dos cloridratos dos α-amino ésteres 2a-d e dos compostos 1,3-dicarbonílicos 3a,b e 5 em presença de trietilamina. Estes compostos foram preparados empregando energia de microondas, sem uso de solvente, utilizando como suporte sólido K-10 ou KSF e também foram efetuadas re...
متن کاملIsothiourea-catalyzed asymmetric synthesis of β-lactams and β-amino esters from arylacetic acid derivatives and N-sulfonylaldimines.
The isothiourea HBTM-2.1 (5 mol %) catalyzes the asymmetric formal [2 + 2] cycloaddition of both arylacetic acids (following activation with tosyl chloride) and preformed 2-arylacetic anhydrides with N-sulfonylaldimines, generating stereodefined 2,3-diaryl-β-amino esters (after ring-opening) and 3,4-diaryl-anti-β-lactams, respectively, with high diastereocontrol (up to >95:5 dr) and good to exc...
متن کاملTin(II) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement.
A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(II) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
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ژورنال
عنوان ژورنال: Arkivoc
سال: 2009
ISSN: 1551-7012
DOI: 10.3998/ark.5550190.0010.b09