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Please login to access the full content or check if you have access via Method 2: Nucleophilic Ring Opening of Oxetanes

DOI: 10.1055/sos-SD-036-00701

Bingham, M. J.; Greaney, M. F.Science of Synthesis, (2008361013.

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.[‌254‌‌260‌] 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] [‌254‌‌257‌] 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.

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Meeeeeeeeeee Meeeeeeee

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

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

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