A1 Journal article (refereed)
Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones (2020)


Csókás, Dániel; Siitonen, Juha H.; Pihko, Petri M.; Pápai, Imre (2020). Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones. Organic Letters, 22 (12), 4597-4601. DOI: 10.1021/acs.orglett.0c01008


JYU authors or editors


Publication details

All authors or editors: Csókás, Dániel; Siitonen, Juha H.; Pihko, Petri M.; Pápai, Imre

Journal or series: Organic Letters

ISSN: 1523-7060

eISSN: 1523-7052

Publication year: 2020

Volume: 22

Issue number: 12

Pages range: 4597-4601

Publisher: American Chemical Society

Publication country: United States

Publication language: English

DOI: http://doi.org/10.1021/acs.orglett.0c01008

Open Access: Open access publication published in a hybrid channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/70921


Abstract

A stereoselectivity model inspired by the total synthesis of stemona alkaloids is developed to explain why enolate-derived 3,4-fused butyrolactones are methylated with a preference for syn alkylation. The model shows how conformational locking present in nonplanar enolate structures favors syn over anti methylation, due to less significant structural distortions in the syn pathway. The developed model was also successfully used to rationalize selectivities of previously documented methylation reactions.


Keywords: organic compounds; alkaloids; isomerism; chemical reactions

Free keywords: chemical structure; enolates; transition states; selectivity; organic reactions


Contributing organizations


Ministry reporting: Yes

Reporting Year: 2020

Preliminary JUFO rating: 2


Last updated on 2020-18-08 at 13:42