A convenient large-scale chiral synthesis of protected 2-substituted 4-oxo-piperidine derivatives
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A convenient large-scale chiral synthesis of protected 2-substituted-4-oxo-piperidine derivatives is described. Hetero Diels-Alder reaction between trifluoroacetic acid-boron trifluoride activated (1-phenyl-ethylimino)acetic acid ethyl ester and 2-trimethylsilyloxy-1,3-butadiene gave rise to a mixture of two diastereomers of 4-oxo-1-(1-phenyl-ethyl)-piperidine-2-carboxylic acid ethyl ester. Starting from (S)-1-phenyl-ethylamine pure adduct can be obtained by crystallization of the diastereomeric mixture. Reduction of the ester group gave rise to the corresponding hydroxymethyl analogue, which was subjected to further functional group transformations to yield the desired protected 2-aminomethyl-4-oxo-piperidine derivative without any racemization being observed.
Original language | English |
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Journal | Tetrahedron |
Volume | 58 |
Issue number | 36 |
Pages (from-to) | 7339-7344 |
Number of pages | 6 |
ISSN | 0040-4020 |
DOIs | |
Publication status | Published - 2 Sep 2002 |
- Amino acids and derivatives, Diels-Alder reactions, Piperidinones
Research areas
ID: 382746837