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. 2022 Mar 25;12(16):9519–9523. doi: 10.1039/d2ra01315k

Ring-opening of the compound 5.

graphic file with name d2ra01315k-u2.jpg
Entry Solvent Temperature Reagents Yield
1 THF 0 °C LDA Decom.
2 DME r.t. Li, EDAa Decom.
3 DME 0 °C Li, EDA Decom.
4 CH3CN r.t. Anhydrideb 8, 98% (trans : cis = 3 : 2)
5 THF −78 °C to 0 °C LHMDS, MeOTf Decom.
6 THF −78 °C to 0 °C LDA, MeOTf Decom.
a

Ethylenediamine.

b

Acetic toluene-p-sulfonic anhydride, prepared by acetyl chloride and PTSA.25