Amino Acids as a Chiral Pool: Synthesis of (S)‐and (R)‐2‐N‐Carbomethoxy‐5‐aminoindane from (S)‐ and (R)‐Phenylalanines

Autor:	Andrew Bach, Oljan Repic, Joseph Mckenna, Thomas J. Blacklock, Liladhar Murlidhar Waykole, Mahavir Prashad
Rok vydání:	2007
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Chiral pool synthesis Chemistry Stereochemistry Nitration Organic Chemistry Enantioselective synthesis Regioselectivity Phenylalanine Amino acid
Zdroj:	Synthetic Communications. 37:1445-1454
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397910701226905
Popis:	Enantioselective syntheses of (R)‐and (S)‐2‐N‐carbomethoxy‐5‐aminoindanes from (R)‐ and (S)‐phenylalanines, respectively, are described. A Friedel–Crafts reaction employing N‐carbomethoxy phenylalanine leads to chiral 2‐N‐carbomethoxy‐1‐indanone, which is diastereoselectively reduced to 1‐hydroxy‐2‐N‐carbomethoxyindane. After protection of the hydroxyl group, a regioselective nitration gives a 6‐nitroindane intermediate, which upon hydrogenation affords (R)‐or (S)‐2‐N‐carbomethoxy‐5‐aminoindane.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a345b1042d55822c97267a7abca5a2b2 https://doi.org/10.1080/00397910701226905 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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