Реакция Анри

Реакция Генри (Анри)[1], нитроальдольная реакция (англ. Henry reaction, nitroaldol reaction) — реакция альдольного типа между альдегидом и нитрометаном.

Стадия нуклеофильного присоединения катализируется основаниями и, в случае наличия кислого протона в альфа-положении, может сопровождаться элиминированием воды. Основными продуктами реакции Анри являются бета-гидроксинитросоединения, побочными — нитроалкены (особенно в случае использования ароматических альдегидов).

Особенности

Особенности реакции Анри[2]:

Стереоселективность

Так как в реакции Анри образуется до двух новых стереоцентров, теоретически возможно образование до 4 стереоизомерных продуктов. Обычно образуется смесь диастереомеров, хотя применение хиральных лигандов позволяет увеличить выход одного (или нескольких) из них. Например, каталитическая система, состоящая из соли трифлата цинка, основания диизопропилэтиламина (DIPEA) и хирального лиганда (+)-N-метилэфедрина (NME), позволяет получить продукт энантиоселективной конденсации бензальдегида и нитрометана[3].

Более сложный пример диастереоселективной реакции Анри показан ниже.[4]

Примечания

  1. ↑ Henry, L. C. R. Hebd. Acad. Sci. 1895, 120, 1265.
  2. ↑ Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Academic Press: 2005
  3. ↑ Enantioselective Henry Reactions under Dual Lewis Acid/Amine Catalysis Using Chiral Amino Alcohol Ligands Claudio Palomo, Mikel Oiarbide, Antonio Laso Angewandte Chemie, Vol. 44, Issue 25 , P. 3881 — 3884 2005 Abstract (недоступная ссылка)
  4. ↑ Organocatalyzed diastereoselective Henry reaction of enantiopure 4-oxoazetidine-2-carbaldehydes Benito Alcaide, Pedro Almendros, Amparo Luna, M. Paz de Arriba and M. Rosario Torresc ARKIVOC 2007 (iv) 285—296

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