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).