A De Novo Stereocontrolled Approach to syn- and anti-Disubstituted Acyclic β2,3-Amino Acid Enantiomers

Cherepanova, Maria and Kiss, Loránd and Forró, Enikő and Fülöp, Ferenc (2014) A De Novo Stereocontrolled Approach to syn- and anti-Disubstituted Acyclic β2,3-Amino Acid Enantiomers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. pp. 403-409. ISSN 1434-193X

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Abstract

The stereocontrolled syntheses of functionalized acyclic β2,3- amino acid derivatives in enantiomerically pure form were performed by starting from enantiopure cis- and trans-2- aminocyclopent-3-enecarboxylates, which were derived from a racemic bicyclic β-lactam. The synthetic strategy involves the stereoselective dihydroxylaton of the C–C double bond of the cyclopentene β-amino esters. The subsequent NaIO4-mediated ring cleavage affords dialdehyde intermediates that undergo functionalization by a Wittig reaction.

Item Type:	Article
Uncontrolled Keywords:	Synthetic methods / Amino acids / Kinetic resolution / Diastereoselectivity / Wittig reactions / Lactams
Subjects:	Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User:	Dr Loránd Kiss
Date Deposited:	11 Sep 2014 12:31
Last Modified:	12 Sep 2014 08:11
URI:	http://real.mtak.hu/id/eprint/14730

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• A De Novo Stereocontrolled Approach to syn- and anti-Disubstituted Acyclic β2,3-Amino Acid Enantiomers. (deposited 10 Sep 2014 12:29)
  • A De Novo Stereocontrolled Approach to syn- and anti-Disubstituted Acyclic β2,3-Amino Acid Enantiomers. (deposited 11 Sep 2014 12:31) [Currently Displayed]

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