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Synthesis 2005(3): 425-428
DOI: 10.1055/s-2004-834953
DOI: 10.1055/s-2004-834953
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of an Enantiopure Fluorous 1,2-Diphenyl-1,2-diaminoethane
Further Information
Received
11 October 2004
Publication Date:
08 December 2004 (online)
Publication History
Publication Date:
08 December 2004 (online)
Abstract
Enantiopure fluorous 1,2-diphenyl-1,2-ethanediamine bearing four fluorous ponytails and having 62.2% fluorine content has been prepared. Resolution of racemic 1,2-bis(3,5-dimethoxyphenyl)ethane-1,2-diamine with (-)-menthyl chloroformate followed by reduction of the obtained carbamate afforded the corresponding enantiopure secondary diamines. Protection of the amino function as an aminal, followed by the cleavage of the methoxy moiety and then the introduction of the four fluorous ponytails gave after hydrolysis the enantiopure fluorous 1,2-diphenyl-1,2-ethanediamine.
Key words
enantiopure fluorous diamine - C2 axis - resolution
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