Skip to main content
. 2022 Mar 21;24(12):2365–2370. doi: 10.1021/acs.orglett.2c00568

Scheme 1. Annulation of Oxetanols and 1,2-Diols for the One-Pot Formation of 1,4-Dioxanes.

Scheme 1

Reactions on a 0.25 mmol scale unless otherwise stated. Isolated yields are reported. Diastereomeric (dr) and regioisomeric (rr) ratios determined from the 1H NMR spectrum of the crude reaction mixture.

Reaction run on a 5.5 mmol scale.

Reaction run on a 0.22 mmol scale.

18% of phenol 8 was also isolated.

Reaction run for 32 h.

Reaction run on a 0.136 mmol scale and the product isolated as a mixture of regioisomers with the indicated rr.

Product isolated as a mixture of diastereomers with the indicated dr.

An additional 11% of a diastereomeric mixture was isolated (dr 67:33).

Reaction run at 50 °C.

Additional 10% of a diastereomeric mixture was isolated (dr 26:74).

Additional 20% of a diastereomeric mixture was isolated (dr 39:61).

Reaction run at 0–30 °C and using 1.2 equiv of bis-nucleophile (see Supporting Information Table S3).

Reaction run on a 0.38 mmol scale (oxetanol) at 0–23 °C and using 0.75 equiv of bis-nucleophile (see Supporting Information Table S4). Yield based on bis-nucleophile.

Using TfOH (5 mol %) in CHCl3 (0.5 M) at 25 °C (see Supporting Information Table S5).