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. Author manuscript; available in PMC: 2019 Feb 19.
Published in final edited form as: Tetrahedron. 2015 Mar 20;71(21):3507–3514. doi: 10.1016/j.tet.2015.03.052

Scheme 4. Comparison of the oxidation methods.

Scheme 4

Reagents and conditions: (a) LiAlH4, THF, 0 °C; (b) Swern [(COCl)2, DMSO, Et3N, DCM, −78 °C]; (c) Parikh-Doering [Py•SO3, DMSO/DCM (1/1), Et3N, 0 °C→rt]; (d) NaBH3CN, MeOH, 0 °C→rt; (e) 5% m-cresol, TFA, DCM, rt; (f) MTPA-Cl, DIPEA, DCM 0 °C→rt; (g) glycine ethyl ester, MeOH, 4 °C, then acetic acid, NaBH3CN.