Journal
HETEROCYCLES
Volume 80, Issue 1, Pages 125-131Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-09-S(S)27
Keywords
Methylenebutyrolactam; Indium; Sulfinylimine; Stereoselective Synthesis; Ethyl 2-Bromoethylacrylate
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Funding
- Spanish Ministerio de Educacion y Ciencia (MEC) [2010-CSD2007-00006, CTQ-2007-65218]
- Generalitat Valenciana
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The reaction of ethyl 2-(bromomethyl)acrylate (1) with chiral N-tert-butylsulfinyl aldimines 2 and indium powder in THF at 100 degrees C for 48 h affords, after hydrolysis, a mixture of N-tert-butylsulfinyl aminoesters 3 and alpha-methylene-gamma-butyrolactams 4. From the reaction mixture, compounds 3 were quantitatively converted to the expected butyrolactams 4 after removal of the tert-butylsulfinyl group under acidic conditions and final basic workup. The whole process takes place in high overall yields and with fairly good stereoselectivities.
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