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Amino Acids
,  том 46 ,  издание 4 ,  страницы 1097-1103

Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation–alkylation sequence of a chiral γ-lactam

Тип публикации: Journal Article
Дата публикации: 2014-01-28
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ISSN: 09394451, 14382199
Organic Chemistry
Biochemistry
Clinical Biochemistry
Краткое описание
Starting from a chiral 4-hydroxymethyl pyrrolidin-2-one, an isostere of α-methyl homoserine tethered on a γ-lactam ring was prepared exploiting a stereoselective acylation–methylation sequence, followed by Curtius rearrangement, and structural assignment was confirmed by n.O.e. experiments. By reverting the sequence, the 3-carboxy-3-methyl derivative having the opposite configuration at C-3 was obtained with total stereoselection, but Curtius rearrangement invariably afforded only inseparable mixtures of decomposition products.
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Civitavecchia A. et al. Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation–alkylation sequence of a chiral γ-lactam // Amino Acids. 2014. Vol. 46. No. 4. pp. 1097-1103.
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Civitavecchia A., Martelli G., Orena M., Rinaldi S. Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation–alkylation sequence of a chiral γ-lactam // Amino Acids. 2014. Vol. 46. No. 4. pp. 1097-1103.
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TY - JOUR
DO - 10.1007/s00726-014-1671-9
UR - http://link.springer.com/10.1007/s00726-014-1671-9
TI - Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation–alkylation sequence of a chiral γ-lactam
T2 - Amino Acids
AU - Civitavecchia, Annafelicia
AU - Martelli, Gianluca
AU - Orena, Mario
AU - Rinaldi, Samuele
PY - 2014
DA - 2014/01/28
PB - Springer Nature
SP - 1097-1103
IS - 4
VL - 46
PMID - 24468930
SN - 0939-4451
SN - 1438-2199
ER -
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@article{2014_Civitavecchia,
author = {Annafelicia Civitavecchia and Gianluca Martelli and Mario Orena and Samuele Rinaldi},
title = {Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation–alkylation sequence of a chiral γ-lactam},
journal = {Amino Acids},
year = {2014},
volume = {46},
publisher = {Springer Nature},
month = {jan},
url = {http://link.springer.com/10.1007/s00726-014-1671-9},
number = {4},
pages = {1097--1103},
doi = {10.1007/s00726-014-1671-9}
}
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Civitavecchia, Annafelicia, et al. “Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation–alkylation sequence of a chiral γ-lactam.” Amino Acids, vol. 46, no. 4, Jan. 2014, pp. 1097-1103. http://link.springer.com/10.1007/s00726-014-1671-9.