Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water
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.
Keywords:
aldehydes / cyclopentadiene / trifluoroacetic acid / toluene / waterSource:
Organic Letters, 2022, 24, 40, 7455-7460Publisher:
- USA : American Chemical Society
Funding / projects:
- Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)
- The Japan Society for the Promotion of Science (grant Japan 19H05630)
DOI: 10.1021/acs.orglett.2c03043
ISSN: 1523-7060
PubMed: 36190808
WoS: 000879214700001
Scopus: 2-s2.0-85139421716
Collections
Institution/Community
IHTMTY - 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 . .