Stereoselective Synthesis of Conjugated Fluoro Enynes
In: Journal of organic chemistry, Jg. 77 (2012), Heft 19, S. 8417-8427
academicJournal
- print, 26 ref
Zugriff:
Metalation―etectrophilic fluorination of TMS- and TIPS-protected 1,3-benzothiazol-2-yl (BT) propargyl sulfones gave corresponding BT fluoropropargyl sulfones, Julia―Kocienski reagents for the synthesis of fluoro enynes. Both reagents reacted with aldehydes under mild DBU- or LHMDS-mediated conditions, giving high yields of conjugated fluoro enynes with E-stereoselectivity. In comparison to DBU-mediated reactions, stereoselectivity was higher in low-temperature LHMDS-mediated reactions. Two ketones were shown to react as well, using LHMDS as base. In situ removal of the TMS group gave terminal conjugated 2-fluoro 1,3-enynes. Synthetic utility of the fluoro enynes was demonstrated by conversion to internal alkynes and to stereoisomeric fluoro dienes via Sonogashira and Heck couplings.
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Stereoselective Synthesis of Conjugated Fluoro Enynes
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Autor/in / Beteiligte Person: | KUMAR, Rakesh ; ZAJC, Barbara |
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Zeitschrift: | Journal of organic chemistry, Jg. 77 (2012), Heft 19, S. 8417-8427 |
Veröffentlichung: | Washington, DC: American Chemical Society, 2012 |
Medientyp: | academicJournal |
Umfang: | print, 26 ref |
ISSN: | 0022-3263 (print) |
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