A convenient approach to enantiomerically pure 4-hydroxymethyl- 3-phenoxy-2-azetidinone has been carried out using the easily available aldehyde 5 as chiral starting material.

Synthesis of optically pure 4-hydroxymethyl-3-phenoxy-2-azetidinone from D-glucal

Glycal-derived δ-hydroxy α,β-unsaturated aldehydes (Perlin aldehydes): versatile building blocks in organic synthesis.

Synthesis of Optically Pure 4‐Hydroxymethyl‐3‐phenoxy‐2‐azetidinone (VIII) from D‐Glucal (I).

In the last two decades, the better understanding of the mechanistic aspects of the β-lactams biological activity and their inhibition, and the chemical exploitation of β-lactams as synthetic intermediates in organic chemistry, have experienced a continuous and somewhat complementary advance. A prerequisite for such a development has been the accessibility of enantiopure β-lactams. The latter are now routinely prepared most often through the ketene-imine cycloaddition reaction, also termed the Staudinger reaction. This review accounts for the recent progress made in the asymmetric synthesis of β-lactams (with special emphasis in the Staudinger reaction approach), as well as in their use as synthetic intermediates en route to natural products, including α- and β-amino acids and peptides derived therefrom.

Synthesis of optically pure 4-hydroxymethyl-3-phenoxy-2-azetidinone from D-glucal

Citations

Glycal-derived δ-hydroxy α,β-unsaturated aldehydes (Perlin aldehydes): versatile building blocks in organic synthesis.

Synthesis of Optically Pure 4‐Hydroxymethyl‐3‐phenoxy‐2‐azetidinone (VIII) from D‐Glucal (I).

References

Asymmetric Synthesis of β-Lactams Through the Staudinger Reaction and Their Use as Building Blocks of Natural and Nonnatural Products

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