The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.
TY - JOUR
AU - Marjanovic, Jasna
AU - Divjakovic, Vladimir
AU - Matović, Radomir
AU - Ferjančić, Zorana
AU - Saičić, Radomir N.
PY - 2013
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1215
AB - The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.
PB - Wiley-V C H Verlag Gmbh, Weinheim
T2 - European Journal of Organic Chemistry
T1 - Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)
VL - 2013
IS - 25
SP - 5555
EP - 5560
DO - 10.1002/ejoc.201300716
UR - Conv_3015
ER -
@article{
author = "Marjanovic, Jasna and Divjakovic, Vladimir and Matović, Radomir and Ferjančić, Zorana and Saičić, Radomir N.",
year = "2013",
abstract = "The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)",
volume = "2013",
number = "25",
pages = "5555-5560",
doi = "10.1002/ejoc.201300716",
url = "Conv_3015"
}
Marjanovic, J., Divjakovic, V., Matović, R., Ferjančić, Z.,& Saičić, R. N.. (2013). Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1). in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim., 2013(25), 5555-5560.
https://doi.org/10.1002/ejoc.201300716
Conv_3015
Marjanovic J, Divjakovic V, Matović R, Ferjančić Z, Saičić RN. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1). in European Journal of Organic Chemistry. 2013;2013(25):5555-5560.
doi:10.1002/ejoc.201300716
Conv_3015 .
Marjanovic, Jasna, Divjakovic, Vladimir, Matović, Radomir, Ferjančić, Zorana, Saičić, Radomir N., "Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)" in European Journal of Organic Chemistry, 2013, no. 25 (2013):5555-5560,
https://doi.org/10.1002/ejoc.201300716 .,
Conv_3015 .
