| Tartalom: |
http://real.mtak.hu/31587/ |
| Archívum: |
MTA Könyvtár |
| Gyűjtemény: |
Status = Published
Type = Article
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| Cím: |
Asymmetric synthesis of ?,?-diamino acid derivatives with an aziridine-,
azetidine- and ?-lactone-skeleton via Mannich-type additions across ?-chloro-
N-sulfinylimines
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| Létrehozó: |
Callebaut, Gert
Mangelinckx, Sven
Kiss, Loránd
Sillanpää, Reijo
Fülöp, Ferenc
De Kimpe, Norbert
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| Dátum: |
2012
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| Téma: |
QD04 Organic chemistry / szerves kémia
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| Tartalmi leírás: |
The efficient asymmetric synthesis of new chiral ?-chloro-?,?-diamino acid derivatives via highly
diastereoselective Mannich-type reactions of N-(diphenylmethylene) glycine esters across a chiral
?-chloro-N-p-toluenesulfinylimine was developed. The influence of the base, LDA or LiHMDS, used for
the formation of the glycine enolates, was of great importance for the anti-/syn-diastereoselectivity of the
Mannich-type reaction. The ?-chloro-?,?-diamino acid derivatives proved to be excellent building blocks
for ring closure towards optically pure anti- and syn-?,?-aziridino-?-amino esters, and subsequent ring
transformation into trans-3-aminoazetidine-2-carboxylic acid derivatives and ?,?-diamino-
?-butyrolactones.
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| Típus: |
Article
PeerReviewed
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| Formátum: |
text
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| Azonosító: |
Callebaut, Gert and Mangelinckx, Sven and Kiss, Loránd and Sillanpää, Reijo and Fülöp, Ferenc and De Kimpe, Norbert (2012) Asymmetric synthesis of ?,?-diamino acid derivatives with an aziridine-, azetidine- and ?-lactone-skeleton via Mannich-type additions across ?-chloro- N-sulfinylimines. Organic and Biomolecular Chemistry, 10. pp. 2326-2338. ISSN 1477-0520, ESSN: 1477-0539
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