Abstract
A one-pot transformation, which involves the reaction of ketones with aldehydes in the presence of metal halides to furnish tetrahydro-2H-pyran-2,4-diols in a highly diastereoselective manner, is investigated thoroughly by experiments and computations. The reaction was also successfully implemented on a flow micro reactor system.
Highlights
Since its discovery in the late nineteenth century the aldol reaction has become one of the most powerful tools in the field of carbon–carbon bond formation [1,2,3,4,5]
The enolate was generated from propiophenone by deprotonation with lithium diisopropylamide (LDA) at −40 °C in tetrahydrofuran (THF)
The resulting metal enolate was treated with a stoichiometric amount of benzaldehyde (3a) and stirred for 2 h at 0 °C, room temperature or 67 °C
Summary
Since its discovery in the late nineteenth century the aldol reaction has become one of the most powerful tools in the field of carbon–carbon bond formation [1,2,3,4,5]. It is widely used in the formation of many natural products [6,7,8,9,10,11], stereoselective syntheses [12,13,14,15,16], and tandem reactions [17,18,19]. Scheme 1: Synthesis of racemic tetrahydro-2H-pyran-2,4-diols rac-5 from enolates 2 and aldehydes 3
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