199125-42-3Relevant academic research and scientific papers
Iodomethylation of Chiral α-Amino Aldehydes by Means of Samarium/Diiodomethane. Application to the Synthesis of Various Enantiomerically Pure Compounds
Concellon, Jose M.,Bernad, Pablo L.,Perez-Andres, Juan A.
, p. 8902 - 8906 (1997)
Chiral iodohydrins 2 have been obtained from α-amino aldehydes 1 and Sm/CH2I2. Treatment of compound 2 with acetic anhydride, NaH, or AgBF4 affords, with high diastereoselectivity, O-protected 3-(dibenzylamino)-1-iodoalkan-2-ol 3, amino epoxides 4, or azetidinium salts 5, respectively. The synthesis of enantiomerically pure allylamines 6 is also described by metallation of 3 with zinc. The reaction of α-amino aldehydes 1 with Sm/CH2I2 and further treatment with organocuprates affords chiral amino alcohols 7 in a one-pot process.
Nucleophilic ring closure and opening of aminoiodohydrins
Concellón, José M.,Bernad, Pablo L.,Pérez-Andrés, Juan A.
, p. 1231 - 1234 (2007/10/03)
Enantiopure aminoiodohydrins obtained from α-aminoaldehydes and Sm/CH2I2 have been transformed into regioisomeric aminoiodohydrins, aminoepoxides, azetidines or 1,3-oxazolidines. The key step in these transformations is a nucleophilic opening-closing process. (C) 2000 Elsevier Science Ltd.
