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. 2022 Dec 7;29(6):e202203375. doi: 10.1002/chem.202203375

Scheme 5.

Scheme 5

Synthesis of the functionalized exo‐TCO carbamate derivatives from the axial and equatorial isomers 7 and 8. 21/22: 7‐amino‐4‐methylcoumarin (1.25 equiv), triphosgene (1.25 equiv.), DIPEA (4.6 equiv.), DMAP (3.0 equiv.), toluene, DCM, 21 °C, 18 h, 42–63 %. 23/24: i. DPFPC (2.0 equiv.), DIPEA (5.0 equiv.), DMAP (0.1 or 5.0 equiv.), MeCN. ii. glycine methyl ester hydrochloride (5.0‐7.0 equiv.), DIPEA (2.5‐4.5 equiv.), MeCN, 21 °C, 18 h, 27–42 %. 25/26 i. DPFPC (2.0 equiv.), DIPEA (5.0 equiv.), DMAP (0.1 equiv.), MeCN. ii. sarcosine methyl ester hydrochloride (2.0 equiv.), DIPEA (2.5 equiv), MeCN, 21 °C, 18 h, 25–31 %.