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Synthesis 2008(22): 3670-3674  
DOI: 10.1055/s-0028-1083211
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Improved Robust Method for Preparing Optically Active 3-Alkyl-3-phenyl-1,4-dioxane-2,5-diones; A Promising New Chiral Template

Ryohei Nagase, Yuuki Iida, Mikiko Sugi, Tomonori Misaki, Yoo Tanabe*
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyougo 669-1337, Japan
Fax: +81(79)5659077; e-Mail: tanabe@kwansei.ac.jp;
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Publication History

Received 23 June 2008
Publication Date:
29 October 2008 (online)

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Abstract

A robust method for preparing (3S)-3-alkyl-3-phenyl-1,4-dioxane-2,5-diones was developed using an improved cyclocondensation reaction between (S)-α-alkylmandelic acids and 2-bromocarbonyl halides. Subtle differences in the reaction conditions, including separate additions of triethylamine, significantly increased the yield compared with Schöllkopf’s original method.

Key words

1,4-dioxan-2,5-diones - cyclocondensation - α-alkylmandelic acids - chiral template

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8

Direct formation of 5B from (S)-4a (not through 5A) might be considered. However, we speculate that this reaction does not proceed because carboxylate anion of (S)-4a has higher reactivity than the tertiary hydroxy group.