The important naturally occurring beta-amino acid N-Boc-ADDA is prepared following a disconnection of the C-C bond between the two E,E double bonds. The stereochemistry of the two synthons was controlled using the alkylation of chiral bromoalienes derived from naturally occurring (S)-serine and (S)-phenyllactic acid. The cupration of bromoallenes derived from (S)-serine also provides a general method for the synthesis of chiral beta-alkylated aspartic acid derivatives. (C) 1997, Elsevier Science Ltd.
Daniello, F., Mann, A., Schoenfelder, A., Taddei, M. (1997). Stereoconvergent synthesis of (2S,3S,8S,9S,4E,6E)-N-Boc-ADDA starting from (S)-serine and (S)-phenyllactic acid. TETRAHEDRON, 53(4), 1447-1456 [10.1016/S0040-4020(96)01056-3].
Stereoconvergent synthesis of (2S,3S,8S,9S,4E,6E)-N-Boc-ADDA starting from (S)-serine and (S)-phenyllactic acid
Taddei, Maurizio
1997-01-01
Abstract
The important naturally occurring beta-amino acid N-Boc-ADDA is prepared following a disconnection of the C-C bond between the two E,E double bonds. The stereochemistry of the two synthons was controlled using the alkylation of chiral bromoalienes derived from naturally occurring (S)-serine and (S)-phenyllactic acid. The cupration of bromoallenes derived from (S)-serine also provides a general method for the synthesis of chiral beta-alkylated aspartic acid derivatives. (C) 1997, Elsevier Science Ltd.
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https://hdl.handle.net/11365/31464
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