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Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water
A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.
Keywords:
aldehydes / cyclopentadiene / trifluoroacetic acid / toluene / water
TY - JOUR
AU - Bondžić, Bojan
AU - Daskalakis, Konstantinos
AU - Taniguchi, Tohru
AU - Monde, Kenji
AU - Hayashi, Yujiro
PY - 2022
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/5417
AB - A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.
PB - USA : American Chemical Society
T2 - Organic Letters
T1 - Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water
VL - 24
IS - 40
SP - 7455
EP - 7460
DO - 10.1021/acs.orglett.2c03043
ER -
@article{
author = "Bondžić, Bojan and Daskalakis, Konstantinos and Taniguchi, Tohru and Monde, Kenji and Hayashi, Yujiro",
year = "2022",
abstract = "A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.",
publisher = "USA : American Chemical Society",
journal = "Organic Letters",
title = "Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water",
volume = "24",
number = "40",
pages = "7455-7460",
doi = "10.1021/acs.orglett.2c03043"
}
Bondžić, B., Daskalakis, K., Taniguchi, T., Monde, K.,& Hayashi, Y.. (2022). Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water. in Organic Letters
USA : American Chemical Society., 24(40), 7455-7460.
https://doi.org/10.1021/acs.orglett.2c03043
Bondžić B, Daskalakis K, Taniguchi T, Monde K, Hayashi Y. Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water. in Organic Letters. 2022;24(40):7455-7460.
doi:10.1021/acs.orglett.2c03043 .
Bondžić, Bojan, Daskalakis, Konstantinos, Taniguchi, Tohru, Monde, Kenji, Hayashi, Yujiro, "Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water" in Organic Letters, 24, no. 40 (2022):7455-7460,
https://doi.org/10.1021/acs.orglett.2c03043 . .
