Diastereoselective Ammonium-Directed Epoxidation in the Asymmetric Syntheses of Dihydroconduramines (+)-C-2, (−)-C-2, (+)-D-2, (+)-E-2, (+)-F-2, and (−)-F‑2

• Published in: Journal of organic chemistry Vol. 83; no. 17; pp. 9939 - 9957
• Main Authors: Da Silva Pinto, Solange, Davies, Stephen G, Fletcher, Ai M, Roberts, Paul M, Thomson, James E
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.09.2018; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; GLYCOSIDASE INHIBITORS; DERIVATIVES; PURE; STRATEGY

Epoxidations (40% aq HBF4 then m-CPBA) of racemic cis-2-(N-benzylamino)­cyclohex-3-en-1-ol and racemic cis-2-(N,N-dibenzylamino)­cyclohex-3-en-1-ol proceed with very high levels of diastereoselectivity (>95:5 dr). The latter is in direct contrast to the epoxidation of the corresponding trans-dias...