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Efficient Conversion of Esters to α‐Trimethylsilylketones. Preliminary communication
Author(s) -
Demuth Martin
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610840
Subject(s) - chemistry , trimethylsilyl , primary (astronomy) , ketone , sequence (biology) , organic chemistry , reaction conditions , combinatorial chemistry , catalysis , biochemistry , physics , astronomy
Secondary and tertiary carboxylic methyl or ethyl esters ( 2a‐c ) were converted with trimethylslylmethyllithium ( 3a‐c ) in high yields. Under identical reaction conditions the primary esters 2d,e gave 3d, e in lower yields. Since the trimethylsilyl (TMS) group α to a ketone is known to undergo facile elimination under a variety of reaction conditions, the method also constitutes a highly versatile ester to methylketone sequence.