A rapid access to new fluorinated 1,3-dienes and benzylic fluorides via metathesis on propargylic fluorides

Synlett

Volumn , Issue 16, 2008, Pages 2503-2507

  Pujari, Sandip A ^a   Kaliappan, Krishna P ^a   Valleix, Alain ^b   Grée, Danielle ^c   Grée, René ^c  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b CEA SACLAY   (France)

^c UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Aromatization; Benzylic fluorides; Dehydroxyfluorination; Diels Alder reaction; Enyne metathesis

Indexed keywords

1,3 DIENE DERIVATIVE; ALKADIENE; ETHYLENE; FLUORIDE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

EID: 54249086260     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078179     Document Type: Article

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39. All our attempts to measure the ee values of the intermediates (+)-14 and (+)-15 by NMR in the presence of chiral shift reagents or by chiral HPLC have been unsuccessful so far. This is a well known problem for such chiral monofluorinated molecules, see for instance ref 16a.
40. 2: 230.1846; found: 230.1846.
41. 2 (10 mmol) and the mixture was refluxed for 2 d. After being cooled to r.t., the reaction mixture was passed through a small pad of celite and the filtrate was concentrated and purified by flash column chromatography on silica gel to afford the corresponding aromatized product.
42. 3N (2 g) was added and the mixture was stirred for another 3 h at r.t. The reaction mixture was concentrated and the crude material was purified by column chromatography to afford the corresponding aromatized adducts.
43. 2O, 9:1)