ISSN:
0947-6539
Keywords:
aza-Claisen rearrangement
;
azoniones
;
indolizidinones
;
ring contractions
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The zwitterionic aza-Claisen rearrangement of optically active 3-pyrrolidine acryl esters and various acid chlorides to generate optically active azoninones proceeds with high simple diastereoselectivity (internal asymmetric induction) and a complete 1,3-chirality transfer. The reaction path observed depends on the subsitution pattern of the allylic system: while the more electron-rich alkylated allyl amine fromed predominantly von Braun type products, the α,β-unsaturated esters could be rearranged with high yields. The azoniones thus obtained were treated with electrophiles, inducing regio- and diastereoselective transannular ring contractions. The resulting indolizidinones should be useful key intermediates in alkaloid synthesis.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.1460020719
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