122059-35-2Relevant academic research and scientific papers
Stereocontrolled synthesis and alkylation of cyclic β-amino esters: Asymmetric synthesis of a (-)-sparteine surrogate
Hermet, Jean-Paul R.,Viterisi, Aurelien,Wright, Jonathan M.,McGrath, Matthew J.,O'Brien, Peter,Whitwood, Adrian C.,Gilday, John
, p. 3614 - 3622 (2008/09/21)
A convenient method for the stereoselective synthesis of cyclic β-amino esters from an iodo αβ-unsaturated ester and α-methylbenzylamine is described. Subsequent enolate generation and alkylation proceeds with complete stereocontrol, with the two stereogenic centres working together. In this way, a functionalised piperidine suitable for alkaloid natural product synthesis was prepared. The usefulness of the methodology is exemplified with the concise synthesis of a (-)-sparteine surrogate. The Royal Society of Chemistry.
A New and Practical Procedure for the Bruylants Reaction. Zinc-Mediated Synthesis of Tertiary Homoallylamines and β-Aminoesters
Bernardi, Luca,Bonini, Bianca F.,Capitò, Elena,Dessole, Gabriella,Fochi, Mariafrancesca,Comes-Franchini, Mauro,Ricci, Alfredo
, p. 1778 - 1782 (2007/10/03)
N,N-Disubstituted α-aminonitriles undergo Bruylants reaction under Barbier and Reformatsky conditions with activated halides, in the presence of zinc and 10 mol% HOAc. The high yields and the simple operational conditions make this reaction an appealing, approach to N,N-disubstituted homoallylamines and β-aminoesters.
Synthesis of β-Amino Esters Using the Reformatsky Reaction with α-Amino Nitriles
Dartiguelongue, Caroline,Payan, Steve,Duval, Olivier,Gomes, Luis M.,Waigh, Roger D.
, p. 769 - 772 (2007/10/03)
The chemical behavior of α-amino nitriles towards the Reformatsky reagent has been studied.Under certain conditions, secondary aliphatic α-amino nitrile derivatives yielded a mixture of four products consisting of a β-amino ester, a β-lactam, a bulky tert
Tandem SN2-Michael Reactions for the Preparation of Simple Five- and Six-Membered-Ring Nitrogen and Sulfur Heterocycles
Bunce, Richard A.,Peeples, Christopher J.,Jones, Paul B.
, p. 1727 - 1733 (2007/10/02)
A one-pot tandem SN2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters.Nitrogen-containing rings are prepared by reaction of the ω-halo-2-alkenoate ester with a primary amine in the presence of triethylamine.The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt.Yields are routinely in the 60-80percent range.Experiments are described which elucidate the chronology of the reaction sequences.Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.
A NOVEL OXIDATIVE RING-OPENING REACTION OF ISOXAZOLIDINES: SYNTHESES OF β-AMINO KETONES AND β-AMINO ACID ESTERS FROM SECONDARY AMINES
Murahashi, Shun-Ichi,Kodera, Yoichi,Hosomi, Tatsuhide
, p. 5949 - 5952 (2007/10/02)
A novel oxidative ring-opening reaction of isoxazolidines upon treatment with an electrophile and subsequently with a base gives β-amino ketones and β-amino acid esters highly efficiently.
