F-Butyl lithioacetate

Michael intramolecular alkylation. The reaction of f-butyl lithioacetate (1) with ethyl 6-iodo-2-hexenoate 2 in the presence of potassium t-butoxide in THF at - 78° results in a single trans-1,2-disubstituted cyclopentane (3). Reaction of 2 with f-butyl lithiopropionate (4) under the same conditions results mainly in syn-5, but when HMPT is also present anti-5 is mainly formed. Similar stereoselectivity is observed in reaction of 1 and 4 with ethyl 6-iodo-2-heptenoate in formation of... 

Carbon nucleophiles of type (c) add to the arene ligand and do not rearrange examples include the very reactive anions such as 2-lithio-2-methyl-l,3-dithiane and less sterically encinnbered anions such as lithioacetonitrile and f-butyl lithioacetate. In these cases, the anion adds to an unsubstituted position (mainly ortho or meta to Cl) and does not rearrange. 

P,y-Unsaturated esters. Ruden and Gaffney have prepared j3,7-unsaturated esters by a method based on the facile elimination of trimethylsUanol from 3-hydroxysilanes. Thus reaction of trimethylsilylacetone (1) with f-butyl lithioacetate (2) gives the hydroxy ester (3), which is converted into (4) by treatment with acid. 

IV), and nitriles (V) by reaction with f-butyl lithioacetate, (5, 371), lithio N,N-dimethylacetamide, and lithio acetonitrile, respectively, followed by elimination of trimethylsilanol (Peterson reaction). 

Related Reagents. f-Butyl a-Lithiobis(trimethylsilyl)acetate f-Butyl Trimethylsilylacetate Ethyl Bromozincacetate Ethyl Lithioacetate Ethyl Trimethylsilylacetate Ketene Bis(trimethyl-silyl) Acetal Ketene f-Butyldimethylsilyl Methyl Acetal l-Methoxy-2-trimethylsilyl-l-(trimethylsilyloxy)ethylene Methyl (Methyldiphenylsilyl)acetate Methyl 2-Trimethylsilyl-acrylate Triethyl Phosphonoacetate Trimethylsilylacetic Acid. 

Related Reagents. t-Butyl a-Lithioisohutyrate Dilithio-acetate Ethyl Lithioacetate Ketene Bis(trunethylsilyl) Acetal Ketene f-Butyldimethylsilyl Methyl Acetal l-Methoxy-l-(tri-methylsilyloxy)propene l-Methoxy-2-trunethylsilyl-l-(tri-methylsilyloxy)ethylene Tris(trimethylsilyloxy)ethylene. 

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