Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine. A chiral masked synthon of ethyl formylacetate
Publication type: Journal Article
Publication date: 1999-02-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Deprotonation of chiral masked synthetic equivalents of ethyl glyoxalate, derived from norephedrine, with a novel base formed by addition of tert-BuLi to tert-butyl formate, and subsequent reaction with aromatic aldehydes yields β-hydroxy esters in good yield and moderate to excellent diastereomeric excesses. Reductive transformation of the condensation products, and elimination of the chiral appendage leads to enantiomerically pure 2-aminomethyl-1,3-propanediol derivatives.
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Total citations:
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Citations from 2024:
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(12.5%)
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GOST
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García-Valverde M. et al. Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine. A chiral masked synthon of ethyl formylacetate // Tetrahedron. 1999. Vol. 55. No. 9. pp. 2755-2762.
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Garcı́a-Valverde M., Nieto J., Pedrosa R., Vicente M. Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine. A chiral masked synthon of ethyl formylacetate // Tetrahedron. 1999. Vol. 55. No. 9. pp. 2755-2762.
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TY - JOUR
DO - 10.1016/S0040-4020(99)00046-0
UR - https://doi.org/10.1016/S0040-4020(99)00046-0
TI - Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine. A chiral masked synthon of ethyl formylacetate
T2 - Tetrahedron
AU - Garcı́a-Valverde, Marı́a
AU - Nieto, Javier
AU - Pedrosa, Rafael
AU - Vicente, Martina
PY - 1999
DA - 1999/02/01
PB - Elsevier
SP - 2755-2762
IS - 9
VL - 55
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{1999_García-Valverde,
author = {Marı́a Garcı́a-Valverde and Javier Nieto and Rafael Pedrosa and Martina Vicente},
title = {Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine. A chiral masked synthon of ethyl formylacetate},
journal = {Tetrahedron},
year = {1999},
volume = {55},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/S0040-4020(99)00046-0},
number = {9},
pages = {2755--2762},
doi = {10.1016/S0040-4020(99)00046-0}
}
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MLA
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García-Valverde, María, et al. “Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine. A chiral masked synthon of ethyl formylacetate.” Tetrahedron, vol. 55, no. 9, Feb. 1999, pp. 2755-2762. https://doi.org/10.1016/S0040-4020(99)00046-0.