ChemInform Abstract: Enantioselective Syntheses of Orthogonally Protected Tricarballylic Acid Esters

Autor:	Danilo Giannotti, Silvia Mangani, Enzo Perrotta, Nicholas J. S. Harmat, Maria Altamura, Rossano Nannicini
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Chiral auxiliary Double bond Sodium Enantioselective synthesis chemistry.chemical_element General Medicine Alkylation Hydrolysis chemistry.chemical_compound Enantiopure drug chemistry Succinic acid Organic chemistry
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200020036
Popis:	3( S ) and 3( R )-Benzyloxycarbonyl-pentanedioic acid mono- tert -butyl esters ( 6 ) were obtained as enantiopure orthogonally protected tricarballylic acid (TCA) esters. These were synthesised by alkylation of the sodium enolate derived from chiral but-3-enoyloxazolidinone imides ( 3 ) with tert -butyl bromoacetate; following the hydrolysis to remove the chiral auxiliary, benzyl esterification afforded the 2-allyl succinic acid diesters ( 4 ) that were converted to protected TCA esters after oxidation of the double bond.
Databáze:	OpenAIRE
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