The synthesis of non-racemic β-alkyl-β-aryl-disubstituted allyl alcohols and their transformation into allylamines and amino acids bearing a quaternary stereocenter
| Autor: | Michał Pieczykolan, Sebastian Stecko, Aleksandra Narczyk |
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| Rok vydání: | 2018 |
| Předmět: |
Propanols
Alkylation 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Stereocenter Allylamine chemistry.chemical_compound Nucleophile Physical and Theoretical Chemistry Amino Acids Cyanates Nucleophilic addition 010405 organic chemistry organic chemicals Organic Chemistry Stereoisomerism 0104 chemical sciences Stille reaction chemistry Propargyl Chirality (chemistry) Oxidation-Reduction Isocyanates |
| Zdroj: | Organicbiomolecular chemistry. 16(21) |
| ISSN: | 1477-0539 |
| Popis: | A synthesis of non-racemic β-alkyl-β-aryl allyl alcohols and their transformation into allylamines bearing a quaternary stereogenic center is reported. The allyl alcohols were prepared either by Cu-catalyzed enantioselective reduction of enones or by sequential alkylation/hydrostannylation/Stille coupling of non-racemic propargyl alcohols. The prepared β-alkyl-β-aryl allyl alcohols were converted (after carbamoylation) to the corresponding allylamine derivatives through cyanate-to-isocyanate rearrangement/nucleophilic addition with complete chirality transfer. Varying the nucleophilic agents allowed the preparation of various allylamine derivatives, including carbamates, amides, formamides, ureas, and free amines. The ozonolysis/oxidation of the resulting allylamines provided non-racemic quaternary α-amino acids. |
| Databáze: | OpenAIRE |
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