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A Rapid Access to New Fluorinated 1,3-Dienes and Benzylic Fluorides via Metathesis on Propargylic Fluorides

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Title A Rapid Access to New Fluorinated 1,3-Dienes and Benzylic Fluorides via Metathesis on Propargylic Fluorides
 
Creator PUJARI, SA
KALIAPPAN, KP
VALLEIX, A
GREE, D
GREE, R
 
Subject stereoselective-synthesis
enantioselective synthesis
cross-metathesis
alkyne
strategy
analogs
pressure
reagents
position
route
dehydroxyfluorination
enyne metathesis
diels-alder reaction
aromatization
benzylic fluorides
 
Description The cross enyne metathesis reaction of propargylic fluoride (+)-12 with ethylene affords the enantioenriched 1,3-diene (+)-14 having fluorine-containing side chain at 2-position in good yield. Upon Diels-Alder reaction, followed by aromatization, this diene affords the new benzylic fluorides (+)-16 and (+)-17 in high ee values. This new strategy has been successfully extended to the corresponding gem-difluoro diene 21 and benzylic fluorides 23 and 24.
 
Publisher GEORG THIEME VERLAG KG
 
Date 2011-07-30T07:58:11Z
2011-12-26T12:52:44Z
2011-12-27T05:39:35Z
2011-07-30T07:58:11Z
2011-12-26T12:52:44Z
2011-12-27T05:39:35Z
2008
 
Type Article
 
Identifier SYNLETT, (16), 2503-2507
0936-5214
http://dx.doi.org/10.1055/s-2008-1078179
http://dspace.library.iitb.ac.in/xmlui/handle/10054/7894
http://hdl.handle.net/10054/7894
 
Language en