Tetrahedron Letters

Catalytic monoalkylation of 1, 2-diols

T Maki, N Ushijima, Y Matsumura, O Onomura

Index: Maki, Toshihide; Ushijima, Nobuto; Matsumura, Yoshihiro; Onomura, Osamu Tetrahedron Letters, 2009 , vol. 50, # 13 p. 1466 - 1468

Full Text: HTML

Citation Number: 10

Abstract

A catalytic monoalkylation of 1, 2-diols by using a weak base has been developed. Copper (II) dichloride and boronic acids are effective catalysts for activating 1, 2-diols in the presence of potassium carbonate as a base. Various 1, 2-diols were selectively monoalkylated with allyl-, benzyl-and alkyl-halides in DMF by choosing a suitable catalyst for each 1, 2-diols.

~90%

… Approach to the Synthesis of Taxol. A Synthesis of Optical...

[Mukaiyama, Teruaki; Shiina, Isamu; Sakata, Kaku; Emura, Takayuki; Seto, Keitarou; Saitoh, Masahiro Chemistry Letters, 1995 , # 3 p. 179 - 180]

Enantioselective total synthesis of epothilones A and B usin...

[Sawada, Daisuke; Kanai, Motomu; Shibasaki, Masakatsu Journal of the American Chemical Society, 2000 , vol. 122, # 43 p. 10521 - 10532]

Approaches to the synthesis of enantiopure α-hydroxy-β-lacta...

[Yang, Yan; Wang, Jianmei; Kayser, Margaret Tetrahedron Asymmetry, 2007 , vol. 18, # 17 p. 2021 - 2029]

Catalytic Three??Component Domino Reaction for the Preparati...

[Wachenfeldt, Henrik V.; Roese, Philipp; Paulsen, Filip; Loganathan, Nagarajan; Strand, Daniel Chemistry - A European Journal, 2013 , vol. 19, # 24 p. 7982 - 7988]