Methods for the stereoselective synthesis of 2-fluoroalkenoates. Carbonyl condensation reactions of 3,3-bis(methylthio)-2-fluoropropenal, a highly-functionalized fluoroacrylate cation equivalent

1993 ◽  
Vol 58 (21) ◽  
pp. 5683-5689 ◽  
Author(s):  
Michael C. Pirrung ◽  
Elizabeth G. Rowley ◽  
Christopher P. Holmes
Keyword(s):  
Stereoselective Synthesis ◽  
Condensation Reactions

Stereoselective Synthesis of Bromopiperidinones and their Conversion to Annulated Heterocycles

2009 ◽  
Vol 64 (11-12) ◽  
pp. 1639-1652 ◽  
Author(s):  
Stefan Knauer ◽  
Markus Weymann ◽  
Horst Kunz
Keyword(s):  
Stereoselective Synthesis ◽  
Michael Reaction ◽  
Condensation Reactions ◽  
Cyclic Enaminones

N-Galactopyranosyl- and N-glucopyranosyl imines of aliphatic, aromatic and heteroaromatic aldehydes react with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene in a domino Mannich-Michael reaction cascade to give 2-substituted 5,6-dehydro-piperidin-4-ones with high diastereoselectivity. Treatment of these cyclic enaminones with N-bromo-succinimide yields the corresponding 2-substituted 5-bromo-5,6-dehydropiperidinones which react with L-SelectrideⓇ or methylcuprate to afford the saturated bromo-piperidinones with high diastereoselectivity. Condensation reactions of these products with thioamides afford thiazolopiperidines

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