Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones | Zendy

Dániel Csókás | Zendy; Juha H. Siitonen | Zendy; Petri M. Pihko | Zendy; Imre Pápai | Zendy

Open Access

Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones

Author(s) -

Dániel Csókás,

Juha H. Siitonen,

Petri M. Pihko,

Imre Pápai

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c01008

Subject(s) - chemistry , methylation , stereoselectivity , alkylation , stereochemistry , organic chemistry , catalysis , biochemistry , dna

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.

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