Stereoselective synthesis of N-benzyl (2S,3S,4S)-3-hydroxy-4-methylproline
[Display omitted] The synthesis of (2S,3S,4S)-N-benzyl-3-hydroxy 4-methyl proline and its stereoisomer (2R,3R,4S)-N-benzyl-3-hydroxy 4-methyl proline has been achieved starting with the conjugate addition of methyl methacrolate and benzylamine. The other key reactions performed in our strategy inclu...
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Published in | Tetrahedron: asymmetry Vol. 27; no. 6; pp. 261 - 267 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
01.04.2016
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | [Display omitted]
The synthesis of (2S,3S,4S)-N-benzyl-3-hydroxy 4-methyl proline and its stereoisomer (2R,3R,4S)-N-benzyl-3-hydroxy 4-methyl proline has been achieved starting with the conjugate addition of methyl methacrolate and benzylamine. The other key reactions performed in our strategy include enzymatic separation of an α-methyl β-amino alcohol, Sharpless asymmetric dihydroxylation of an α,β-unsaturated δ-amino ester, and intramolecular cyclization of a sulfonate to a pyrrolidine ring system. Two stereoisomers were synthesized from the common α,β-unsaturated δ-amino ester intermediate. This protocol is simple, straightforward, efficient, highly stereoselective, and economically viable. |
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ISSN: | 0957-4166 1362-511X |
DOI: | 10.1016/j.tetasy.2016.02.008 |