Divergent and Scalable Synthesis of α-Hydroxy/Keto-β-amino Acid Analogues by the Catalytic Enantioselective Addition of Glyoxylate Cyanohydrin to Imines
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چکیده
منابع مشابه
Catalytic enantioselective addition to imines.
Chiral nitrogen-containing compounds are widely distributed in nature and include many biologically important molecules (Chart 1). In these compounds, the nitrogen-containing units are known to play important roles for their bioactivities. For the synthesis of these chiral nitrogen-containing building blocks, use of imines as electrophiles is the most promising and convenient route.1 While many...
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A general, asymmetric synthesis of amino acid derivatives is reported. Masked acyl cyanide (MAC) reagents are shown to be effective umpolung synthons for enantioselective additions to N-Boc-aldimines. The reactions are catalyzed by a modified cinchona alkaloid, which can function as a bifunctional, hydrogen bonding catalyst, and afford adducts in excellent yields (90-98%) and high enantioselect...
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heteropoly acids (hpa) and their salts have advantages as catalysts which make them both economically and environmentally attractive, strong br?nsted acidity, exhibiting fast reversible multi-electron redox transformations under rather mild conditions, very high solubility in polar solvents, fairly high thermal stability in the solid states, and efficient oxidizing ability, so that they are imp...
15 صفحه اولEnantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines.
The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures.
متن کاملStereoselective nucleophilic addition of chiral lithium enolates to (N-tosyl)imines: enantioselective synthesis of -aryl- -amino acid derivatives
Nucleophilic addition of the chiral lithium enolates of (S)-(−)-4-benzyl-2-oxazolidinone acetamide with N-tosyl arylaldehyde imines gives -aryl-amino acid derivatives in good yields and excellent diastereoselectivity. © 2002 Elsevier Science Ltd. All rights reserved. -Amino acids and their derivatives have attracted considerable attention in recent years due to their occurrence in biologically ...
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ژورنال
عنوان ژورنال: ACS Catalysis
سال: 2019
ISSN: 2155-5435,2155-5435
DOI: 10.1021/acscatal.9b03394