Issue 21, 2002

Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran

Abstract

TiCl4–Bu3N-mediated condensation of ketones with α,α-dimethoxyketones afforded trialkylsubstituted 2(5H)-furanones in a one-pot manner, wherein aldol addition and furanone formation occurred sequentially; its application to straightforward synthesis of (R)-mintlactone and (R)-menthofuran, two representative natural mint perfumes, is demonstrated.

Graphical abstract: Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran

Supplementary files

Article information

Article type
Communication
Submitted
16 Aug 2002
Accepted
13 Sep 2002
First published
01 Oct 2002

Chem. Commun., 2002, 2542-2543

Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuran

Y. Tanabe, K. Mitarai, T. Higashi, T. Misaki and Y. Nishii, Chem. Commun., 2002, 2542 DOI: 10.1039/B208077J

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