1376191-77-3Relevant articles and documents
Highly enantioselective synthesis of chiral allenes by sequential creation of stereogenic center and chirality transfer in a single pot operation
Periasamy, Mariappan,Sanjeevakumar, Nalluri,Dalai, Manasi,Gurubrahamam, Ramani,Reddy, Polimera Obula
supporting information; experimental part, p. 2932 - 2935 (2012/08/28)
Chiral allenes are readily accessed in a single pot operation in the reaction of terminal alkynes, aldehydes, chiral secondary amines, and zinc halides in good yields (up to 77% yield) and excellent enantioselectivities (up to 99% ee) in toluene at 120 °C. The reaction proceeds through initial formation of chiral propargylamine intermediates with creation of a new stereogenic center and subsequent chirality transfer via an intramolecular hydride shift to produce chiral allenes with high enantiomeric purities.