Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation

Vulović, Bojan; Trmčić, Milena; Matović, Radomir; Saičić, Radomir

doi:10.1021/acs.orglett.9b03791

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2019

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Abstract

Unsaturated oxyallyl cations with a suitably positioned alkene bond undergo 5-exo-cyclization with the formation of vinylcyclopentane derivatives. Alkyne analogues provide allenes. The reaction proceeds with a moderate to excellent level of stereoselectivity and allows for asymmetric induction in the reaction with chiral substrate.

Source:
Organic Letters, 2019, 21, 23, 9618-9621

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Funding / projects:

The development of new synthetic methods and their application in the synthesis of natural products and biologically active molecules (RS-172027)
Serbian Academy of Sciences and Arts (Project No. F193)
Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)

Note:

Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3841

DOI: 10.1021/acs.orglett.9b03791

ISSN: 1523-7060

WoS: 000502163300071

Scopus: 2-s2.0-85076326919

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	1
	1

TY  - JOUR
AU  - Vulović, Bojan
AU  - Trmčić, Milena
AU  - Matović, Radomir
AU  - Saičić, Radomir
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3819
AB  - Unsaturated oxyallyl cations with a suitably positioned alkene bond undergo 5-exo-cyclization with the formation of vinylcyclopentane derivatives. Alkyne analogues provide allenes. The reaction proceeds with a moderate to excellent level of stereoselectivity and allows for asymmetric induction in the reaction with chiral substrate.
PB  - ACS
T2  - Organic Letters
T1  - Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation
VL  - 21
IS  - 23
SP  - 9618
EP  - 9621
DO  - 10.1021/acs.orglett.9b03791
ER  -

@article{
author = "Vulović, Bojan and Trmčić, Milena and Matović, Radomir and Saičić, Radomir",
year = "2019",
abstract = "Unsaturated oxyallyl cations with a suitably positioned alkene bond undergo 5-exo-cyclization with the formation of vinylcyclopentane derivatives. Alkyne analogues provide allenes. The reaction proceeds with a moderate to excellent level of stereoselectivity and allows for asymmetric induction in the reaction with chiral substrate.",
publisher = "ACS",
journal = "Organic Letters",
title = "Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation",
volume = "21",
number = "23",
pages = "9618-9621",
doi = "10.1021/acs.orglett.9b03791"
}

Vulović, B., Trmčić, M., Matović, R.,& Saičić, R.. (2019). Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation. in Organic Letters
ACS., 21(23), 9618-9621.
https://doi.org/10.1021/acs.orglett.9b03791

Vulović B, Trmčić M, Matović R, Saičić R. Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation. in Organic Letters. 2019;21(23):9618-9621.
doi:10.1021/acs.orglett.9b03791 .

Vulović, Bojan, Trmčić, Milena, Matović, Radomir, Saičić, Radomir, "Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation" in Organic Letters, 21, no. 23 (2019):9618-9621,
https://doi.org/10.1021/acs.orglett.9b03791 . .