The N-Boc derivatives of (2S,3S,4R,6E)-2-amino-3-hydroxy-4-methyl-6-octenoic acid and (2S,4R)-2-amino-4-methyl-hexanoic acid have been prepared using the acetonide of D-Serine aldehyde 1 as a formyl glycine equivalent. The stereochemistry of the y-branch was introduced by reaction of (E)-crotyltrimethylsilane with 1 in the presence of TiCl4 followed by elaboration of the terminal double bond and further transformation of the Serine hydroxymethyl group into a carboxylic acid. Copyright (C) 1996 Elsevier Science Ltd
Daniello, F., Falorni, M., Mann, A., Taddei, M. (1996). Stereocontrolled synthesis of gamma-branched amino acids. TiCl4 mediated addition of (E)-crotylsilane to N,O-protected serine aldehyde. TETRAHEDRON-ASYMMETRY, 7(4), 1217-1226 [10.1016/0957-4166(96)00128-0].
Stereocontrolled synthesis of gamma-branched amino acids. TiCl4 mediated addition of (E)-crotylsilane to N,O-protected serine aldehyde
Taddei, Maurizio
1996-01-01
Abstract
The N-Boc derivatives of (2S,3S,4R,6E)-2-amino-3-hydroxy-4-methyl-6-octenoic acid and (2S,4R)-2-amino-4-methyl-hexanoic acid have been prepared using the acetonide of D-Serine aldehyde 1 as a formyl glycine equivalent. The stereochemistry of the y-branch was introduced by reaction of (E)-crotyltrimethylsilane with 1 in the presence of TiCl4 followed by elaboration of the terminal double bond and further transformation of the Serine hydroxymethyl group into a carboxylic acid. Copyright (C) 1996 Elsevier Science Ltd
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https://hdl.handle.net/11365/31208
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