Preparation of homochiral crown ether containing (S)-1-(1-adamantyl)ethane-1,2-diol as a chiral subunit and its enantioselective complexation with an organic ammonium cation

Koichiro Naemura*, Takashi Mizo-oku, Kimiko Kamada, Keiji Hirose, Yoshito Tobe, Masami Sawada, Yoshio Takai

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Homochiral 1-(1-adamantyl)ethane-1,2-diol (5) was prepared and its absolute configuration was determined to be (S)-(+)-5 by enzymatic and 1H n.m.r. spectroscopic methods. Using (S)-(+)-5 as a chiral subunit, the homochiral crown ether (+)-18 was synthesized and its enantioselectivity in complexation of methionine methyl ester perchlorate was also examined by the 1H n.m.r. spectroscopic method.

Original languageEnglish
Pages (from-to)1549-1558
Number of pages10
JournalTetrahedron: Asymmetry
Volume5
Issue number8
DOIs
StatePublished - 1 Jan 1994

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