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DOI: 10.1055/s-2006-950295
Practical and Robust Method for the Preparation of Seebach and Fráter’s Chiral Template, cis-2-Substituted 5-Methyl(or Phenyl)-1,3-dioxolan-4-ones
Publication History
Publication Date:
09 October 2006 (online)

Abstract
A practical and highly stereoselective method for the preparation of three cis-2-substituted 5-methyl (or phenyl)-1,3-dioxolan-4-ones 3a and 7a (Seebach and Fráter’s chiral template), and a new modified analogue 7b has been developed. The present robust method utilized reactive 2-methoxy-1,3-dioxolane intermediate 4 and the reaction proceeded more smoothly under milder reaction conditions than in previously reported methods. Desired products 3a, 7a, and 7b were easily purified by distillation or recrystallization, i.e. column chromatographic purification, was not necessary.
Key words
(S)-lactic acid - (S)-mandelic acid - cyclocondensation - acid catalyst - 2,5-disubstituted-1,3-dioxolan-4-ones
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1a
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1b
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1c
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1d
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2a
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2b
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2c
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2d
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2e
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3a
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3b
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4a
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4b
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4c
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5a
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References
In our hands, comparable experiments using pentane and heptane (bp 98 °C) as solvents revealed that they have a significant effect on the stereoselectivity; cis/trans = 97:3 (pentane) and 54:46 (heptane). The direct method largely depends on the reaction temperature of azeotropic boiling points.