TMSI-Promoted Diastereoselective Synthesis of 5-(1′-Hydroxy)-γ-butyrolactones

Abstract

Trimethylsilyl iodide (TMSI) was found to be an efficient catalyst for the vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aldehydes with good diastereoselection. The reaction proceeds rapidly in CH₂Cl₂ affording the corresponding 5-(hydroxy(aryl)methyl)furan-2(5H)-ones in good yields. This method offers significant advantages such as efficiency, generality, and mild reaction conditions with shorter reaction time.

Keywords:

• Aldehydes
• butyrolactones
• diastereoselection
• TMSI
• TMSOF

ACKNOWLEDGMENT

MNP thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, for the award of fellowship.

Notes

^a All products were characterized by ¹H NMR, IR, and mass spectral data.