Regioselective Alkyl and Alkynyl Substitution Reactions of Epoxy Alcohols by the Use of Organoaluminum Ate Complexes:  Regiochemical Reversal of Nucleophilic Substitution Reactions

• Published in: Organic letters Vol. 3; no. 11; pp. 1765 - 1767
• Main Authors: Sasaki, Minoru, Tanino, Keiji, Miyashita, Masaaki
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 31.05.2001; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; ASYMMETRIC EPOXIDATION; EPOXIDES

Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl- and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exactly reversed regioselectivity to that obtained in the substitut...