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

2013
journal article
article
10.1002/ejoc.201201413
Journal
European Journal of Organic Chemistry
Author
Nicolas Cyril

Pluta Roman

Pasternak-Suder Monika

Martin Olivier R.

Młynarski Jacek
Volume
2013
Number
7
Pages
1296-1305
ISSN
1434-193X
eISSN
1099-0690
Remarks

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
Scopus© citations
9
cris.lastimport.wos2024-04-09T18:23:38Z
dc.abstract.enAn 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.pl
dc.affiliationWydział Chemii : Zakład Chemii Organicznejpl
dc.contributor.authorNicolas, Cyrilpl
dc.contributor.authorPluta, Romanpl
dc.contributor.authorPasternak-Suder, Monika - 126154 pl
dc.contributor.authorMartin, Olivier R.pl
dc.contributor.authorMłynarski, Jacek - 173385 pl
dc.date.accessioned2015-06-18T08:01:08Z
dc.date.available2015-06-18T08:01:08Z
dc.date.issued2013pl
dc.description.additionalRoman Pluta - Faculty of Chemistry, Jagiellonian Universitypl
dc.description.admin[AB] Pluta, Roman 50000141pl
dc.description.number7pl
dc.description.physical1296-1305pl
dc.description.volume2013pl
dc.identifier.doi10.1002/ejoc.201201413pl
dc.identifier.eissn1099-0690pl
dc.identifier.issn1434-193Xpl
dc.identifier.urihttp://ruj.uj.edu.pl/xmlui/handle/item/9774
dc.languageengpl
dc.language.containerengpl
dc.rights.licenceBez licencji otwartego dostępu
dc.subtypeArticlepl
dc.titleOrganocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal : asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compoundspl
dc.title.journalEuropean Journal of Organic Chemistrypl
dc.typeJournalArticlepl
dspace.entity.typePublication
cris.lastimport.wos
2024-04-09T18:23:38Z
dc.abstract.enpl
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.
dc.affiliationpl
Wydział Chemii : Zakład Chemii Organicznej
dc.contributor.authorpl
Nicolas, Cyril
dc.contributor.authorpl
Pluta, Roman
dc.contributor.authorpl
Pasternak-Suder, Monika - 126154
dc.contributor.authorpl
Martin, Olivier R.
dc.contributor.authorpl
Młynarski, Jacek - 173385
dc.date.accessioned
2015-06-18T08:01:08Z
dc.date.available
2015-06-18T08:01:08Z
dc.date.issuedpl
2013
dc.description.additionalpl
Roman Pluta - Faculty of Chemistry, Jagiellonian University
dc.description.adminpl
[AB] Pluta, Roman 50000141
dc.description.numberpl
7
dc.description.physicalpl
1296-1305
dc.description.volumepl
2013
dc.identifier.doipl
10.1002/ejoc.201201413
dc.identifier.eissnpl
1099-0690
dc.identifier.issnpl
1434-193X
dc.identifier.uri
http://ruj.uj.edu.pl/xmlui/handle/item/9774
dc.languagepl
eng
dc.language.containerpl
eng
dc.rights.licence
Bez licencji otwartego dostępu
dc.subtypepl
Article
dc.titlepl
Organocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal : asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compounds
dc.title.journalpl
European Journal of Organic Chemistry
dc.typepl
JournalArticle
dspace.entity.type
Publication
Affiliations
Wydział Chemii
Pluta, Roman
Młynarski, Jacek
Pasternak-Suder, Monika
No affiliation
Nicolas, Cyril
Martin, Olivier R.

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