Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation
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, 9618-9621Publisher:
- ACS
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
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - 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 . .