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TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions. / Gavrilov, Konstantin N.; Chuchelkin, Ilya V.; Shiryaev, Alexey A. et al.
In: Mendeleev Communications, Vol. 33, No. 6, 01.11.2023, p. 776-778.

Research output: Contribution to journal › Article › peer-review

Harvard

Gavrilov, KN, Chuchelkin, IV, Shiryaev, AA, Firsin, ID, Trunina, VM, Gavrilov, VK, Bityak, YP, Fedorov, DA, Zimarev, VS & Goulioukina, NS 2023, 'TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions', Mendeleev Communications, vol. 33, no. 6, pp. 776-778. https://doi.org/10.1016/j.mencom.2023.10.012

APA

Gavrilov, K. N., Chuchelkin, I. V., Shiryaev, A. A., Firsin, I. D., Trunina, V. M., Gavrilov, V. K., Bityak, Y. P., Fedorov, D. A., Zimarev, V. S., & Goulioukina, N. S. (2023). TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions. Mendeleev Communications, 33(6), 776-778. https://doi.org/10.1016/j.mencom.2023.10.012

Vancouver

Gavrilov KN, Chuchelkin IV, Shiryaev AA, Firsin ID, Trunina VM, Gavrilov VK et al. TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions. Mendeleev Communications. 2023 Nov 1;33(6):776-778. doi: 10.1016/j.mencom.2023.10.012

Author

Gavrilov, Konstantin N. ; Chuchelkin, Ilya V. ; Shiryaev, Alexey A. et al. / TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions. In: Mendeleev Communications. 2023 ; Vol. 33, No. 6. pp. 776-778.

BibTeX

@article{3e0f5dd29d354af09457366e7ac88c04,
title = "TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions",
abstract = "Diastereomeric P,S-bidentate phosphoramidite ligands with TADDOL core and (1R,2S)-1,2-diphenyl-2-(phenylthio)-ethan-1-amine residue were synthesized. These ligands provided up to 76% ee in the Pd-catalyzed alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate, up to 70% ee in the amination of this substrate with pyrrolidine, and 89–95% ee in the Rh-catalyzed asymmetric hydro- genation of dimethyl itaconate and methyl (Z)-2-acetamido-3-arylacrylates. The different contributions of diastereomeric chiral inducers to the catalytic outcome are discussed.",
author = "Gavrilov, {Konstantin N.} and Chuchelkin, {Ilya V.} and Shiryaev, {Alexey A.} and Firsin, {Ilya D.} and Trunina, {Valeria M.} and Gavrilov, {Vladislav K.} and Bityak, {Yan P.} and Fedorov, {Denis A.} and Zimarev, {Vladislav S.} and Goulioukina, {Nataliya S.}",
note = "This work was supported by the Russian Science Foundation (grant no. 19-13-00197) and was performed using NMR equipment of MIPT Shared Facilities Center.",
year = "2023",
month = nov,
day = "1",
doi = "10.1016/j.mencom.2023.10.012",
language = "English",
volume = "33",
pages = "776--778",
journal = "Mendeleev Communications",
issn = "0959-9436",
publisher = "Royal Society of Chemistry",
number = "6",

}

RIS

TY - JOUR

T1 - TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions

AU - Gavrilov, Konstantin N.

AU - Chuchelkin, Ilya V.

AU - Shiryaev, Alexey A.

AU - Firsin, Ilya D.

AU - Trunina, Valeria M.

AU - Gavrilov, Vladislav K.

AU - Bityak, Yan P.

AU - Fedorov, Denis A.

AU - Zimarev, Vladislav S.

AU - Goulioukina, Nataliya S.

N1 - This work was supported by the Russian Science Foundation (grant no. 19-13-00197) and was performed using NMR equipment of MIPT Shared Facilities Center.

PY - 2023/11/1

Y1 - 2023/11/1

N2 - Diastereomeric P,S-bidentate phosphoramidite ligands with TADDOL core and (1R,2S)-1,2-diphenyl-2-(phenylthio)-ethan-1-amine residue were synthesized. These ligands provided up to 76% ee in the Pd-catalyzed alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate, up to 70% ee in the amination of this substrate with pyrrolidine, and 89–95% ee in the Rh-catalyzed asymmetric hydro- genation of dimethyl itaconate and methyl (Z)-2-acetamido-3-arylacrylates. The different contributions of diastereomeric chiral inducers to the catalytic outcome are discussed.

AB - Diastereomeric P,S-bidentate phosphoramidite ligands with TADDOL core and (1R,2S)-1,2-diphenyl-2-(phenylthio)-ethan-1-amine residue were synthesized. These ligands provided up to 76% ee in the Pd-catalyzed alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate, up to 70% ee in the amination of this substrate with pyrrolidine, and 89–95% ee in the Rh-catalyzed asymmetric hydro- genation of dimethyl itaconate and methyl (Z)-2-acetamido-3-arylacrylates. The different contributions of diastereomeric chiral inducers to the catalytic outcome are discussed.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85178100147

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001129586100001

U2 - 10.1016/j.mencom.2023.10.012

DO - 10.1016/j.mencom.2023.10.012

M3 - Article

VL - 33

SP - 776

EP - 778

JO - Mendeleev Communications

JF - Mendeleev Communications

SN - 0959-9436

IS - 6

ER -

ID: 49273490