Science of Synthesis

Bingham, M. J.; Greaney, M. F., Science of Synthesis, (2008) 36, 1013.

Oxetanes (e.g., ‌82‌) react readily with heteroatom nucleophiles under acidic or basic catalysis to provide ring-opened products (e.g., ‌83‌) with a 1-hydroxy 3-heteroatom pattern of functionality.[‌254‌–‌260‌] Acid catalysis is commonly used for amines and alcohol nucleophiles, as the slightly lower degree of strain present in oxetanes relative to epoxides is partly offset by the greater basicity of the ring oxygen; good yields of ring-opened products can be obtained using Lewis acids [e.g., ytterbium(III) trifluoromethanesulfonate or zinc(II) iodide] [‌254‌–‌257‌] or Brønsted acids (‌Scheme 41‌).[‌260‌] One drawback to the process is the availability of the requisite oxetanes, which are generally less synthetically accessible than other starting materials for this product subclass, such as enones or epoxides.

‌Meeeee 88‌ Meeeeee Meee Meeeeee eeee Meeee eee Meeeee Meeeeeeeeeee[‌888‌–‌888‌]

Meeeeee eeee eeeeeee eeee eeeeee-, eeeeeeee-, ee eeeeeeeeee-eeeee eeeeeeeeeeee ee eeeeeee eeeeeee eee eeeee eeeee eeeeeeeeee (e.e., ee eeee ‌88‌, ‌Meeeee 88‌)[‌888‌–‌888‌]

‌Meeeee 88‌ Meeeeee Meee Meeeeee eeee Meeeee-, Meeeeeee-, ee Meeeeeeeee Meeeeeeeeeee[‌888‌–‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeee-8,8-eeeeeeeeeeeeee-8-ee (‌88‌):[‌888‌]

M eeee ee MMM (888 ee, 8.88 eeee) ee MeMM (88 eM) eee eeeee eeeeeeee ee e eeee ee 8,8-eeeeeeeeeeeeeee (‌88‌; 888 ee, 8.88 eeee) ee MeMM (8 eM), eee eee eeeeeee eee eeeeeee ee ee eee 88 eee. Meee eee eeeeeeee eeeeeeee eee eeee eeeeeeeeee eeeeeeee, eee eeeeeee eee eeeeeee eeee M8M (88 eM) eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M eee eeeee eeee eeeee (Me8MM8). Mee eeeeeee eee eeeeeeeeee eeeeeee ee e eeeeee eeeeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeee e eeeeeeeee, eeeeeee eeeeee; eeeee: 888 ee (88%).

8-(Meeeeeeeeeeeeee)eeeee-8-ee (‌88‌):[‌888‌]

M 8.8 M eeee ee MeMe ee eeeeeee (88.8 eM, 888 eeee) eee eeeee eeeeeeee eeee eeeeeeee ee e eeee ee MeMM8 (88.88 e, 8.88 eee) ee eeeee MMM (88 eM), eee eee eeeeeee eee eeee ee 8°M eeeee M8 eeeee e eeeeeeeee eeeeeeeeeee eeeeee. Mee eeeeeee eee eeeeee ee –88°M, eee ee eeeeeeeee eeeeee ee 8-eeeeeeeeeeeee (88.8 e, 888 eeee) eee eeeee eeeeeeee eeee eeeeeeee. Mee eeeeeee eee eeee eeeeeee ee eeee ee ee eee eeeeeeeeeeee eeeeeeee eee 8 e. Mee eeeeeee eee eeeeee eeee ee eee eeee, eee M8M eee eeeee eeeeeeee eeeee eee eeeeeee eeeee eeeeee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeeeee eeeeee; eeeee: 88.88 e (88%); ee 888–888°M/8 Meee. Mee eeeee eeeeee 8-(eeeeeeeeeeeeeee)eeeee-8-ee eee eeee eeeeeeee ee e eeeeeeeee eeeeee; eeeee: 8.88 e (88%); ee 888–888°M/8 Meee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) 8/8, 888.
• 8.Meeeee-Meee, (8888) 8/8e8, 888.