Use of 1, 3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1, 3-dioxines : Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst

Masayuki SATO; Satoshi SUNAMI; Yoshiaki SUGITA; Chikara KANEKO

doi:10.1248/cpb.42.839

Masayuki SATO, Satoshi SUNAMI, Yoshiaki SUGITA, Chikara KANEKO

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Keywords: Mukaiyama aldol reaction, asymmetric aldol reaction, 6-methyl-1, 3-dioxin-4-one, chiral (acyloxy)borane complex, monoacylated tartaric acid-borane complex, goniothalamin

JOURNAL FREE ACCESS

1994 Volume 42 Issue 4 Pages 839-845

DOI https://doi.org/10.1248/cpb.42.839

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Abstract

A novel enantioselective synthesis of 1, 3-dioxin-4-ones having a 2-hydroxylated alkyl group at the 6-position has been accomplished by chiral tartaric acid-derived acylborane-mediated aldol condensation of the silyl enol ether derived from 6-methyl-derivatives of 1, 3-dioxin-4-one with achiral aldehydes.

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