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Synthesis 2009(4): 636-642
DOI: 10.1055/s-0028-1083341
DOI: 10.1055/s-0028-1083341
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A New Class of Tröger’s Base Analogues Bearing Spiro[4.5] Lactone Straps
Further Information
Received
25 September 2008
Publication Date:
27 January 2009 (online)
Publication History
Publication Date:
27 January 2009 (online)
Abstract
A protocol for the introduction of spiro[4.5] lactone straps onto the Tröger’s base scaffold has been developed. The conversion was found to be most efficient when an appropriate carboxylic acid derivative reacted with 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines. Whilst phthaloyl dichloride was the main strap-forming precursor used, other 1,2-unsaturated dicarboxylic acids could be used in the presence of N,N′-dicyclohexylcarbodiimide.
Key words
Tröger’s base - lactones - amines - cyclization - spiro compounds
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