Organocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal : asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compounds

Bibliographic description

punktacja MNiSW [2013 A]: 35

title:	Organocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal : asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compounds
author:	Nicolas Cyril, Pluta Roman, Pasternak-Suder Monika , Martin Olivier R., Młynarski Jacek
journal title:	European Journal of Organic Chemistry
volume:	2013
issue:	7
date of publication :	2013
pages:	1296-1305
ISSN:	1434-193X
eISSN:	1099-0690
DOI:	10.1002/ejoc.201201413
notes:	Roman Pluta - Faculty of Chemistry, Jagiellonian University
language:	English
journal language:	English
abstract in English:	An improved and convenient preparation of protected ( S )- isoserinal on a large scale is reported. This key intermediate was reacted through organocatalyzed aldol reaction or Wittig based chain extension and functionalization to give enantio- pure 1,5,6-trideoxy-1,5-imino-hexitols such as 10a ( L - manno ) and 10b ( D - gluco ). These two compounds are of interest as glycosidase inhibitors. The elaborated organocatalytic pro-cess includes diastereoselective syn aldol reaction of ( S )-iso- serinal hydrate and hydroxyacetone or 1-hydroxy-2-oct- anone and is promoted by various amino acid-based cata- lysts. Diastereoselectivities of up to 8:1 were achieved, thus establishing a new, efficient synthetic route to these impor- tant carbohydrate mimics.
affiliation:	Wydział Chemii : Zakład Chemii Organicznej
type:	journal article
subtype:	academic paper

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