Allylsilane??Modified Amino Acids from the Claisen Rearrangement
M Mohamed, MA Brook
Index: Mohamed, Mustafa; Brook, Michael A. Helvetica Chimica Acta, 2002 , vol. 85, # 12 p. 4165 - 4181
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Citation Number: 13
Abstract
Abstract The Claisen rearrangement of the N-protected, silylated allyl glycinates 11 and 12 led to the formation of allyl/silyl-functionalized amino acids 13 and 14 in yields up to 80%. The diastereoisomer ratio varied from 2: 1 to 29: 1 for 11mb, and from 2: 1 to 46: 1 (syn/anti) for 12mb, depending on reaction conditions, as shown by X-ray crystallographic analysis of 14mb. The relationship between the size of the alkyl groups on the chlorosilane reagent ( ...
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