Diastereoselective Synthesis of γ-Butenolides Catalyzed by Potassium tert-Butoxide

Abstract

Potassium tert-butoxide (0.1 mol%) catalyzed a vinylogous Mukaiyama aldol reaction between aromatic and aliphatic aldehydes with 2-(trimethylsilyloxy)furan. The corresponding γ-butenolides were obtained in good yields with good diastereoselectivities.

GRAPHICAL ABSTRACT

Keywords:

• Butenolides
• 2-(trimethylsilyloxy)furan
• vinylogous Mukaiyama aldol reaction

ACKNOWLEDGMENT

This work was supported by the Start-Up Foundation for Young Scientists of Shihezi University (RCZX200806).

Notes

^a Reaction conditions: 1a (1.2 equiv), 2a (1.0 equiv), ^t BuOK (1 mol %).

^b Yields after purification by column chromatography.

^c syn and anti ratio was determined by ¹H NMR analysis of the crude products.

^d Performed at 0 °C.

^e Performed at −20 °C.

^f 0.1 mol % ^t BuOK was loaded.

^g No ^t BuOK.

^a Reaction conditions: 1a (1.2 equiv), 2 (1.0 equiv), ^t BuOK (0.1 mol %).

^b Yields after purification by column chromatography.

^c syn and anti ratio was determined by ¹H NMR analysis of the crude products.