30011-70-2Relevant academic research and scientific papers
Zinc salt promoted diastereoselective synthesis of chiral propargylamines using chiral piperazines and their enantioselective conversion into chiral allenes
Periasamy, Mariappan,Reddy, Polimera Obula,Edukondalu, Athukuri,Dalai, Manasi,Alakonda, Laxman M.,Udaykumar, Bantu
, p. 6067 - 6076 (2014)
Zinc chloride catalyzed reactions of chiral piperazine derivatives 4a-d with 1-alkynes and aldehydes give chiral propargylamines in 67-95 % yields with up to 99:1 dr. The chiral propargylamines are converted into chiral allenes by using zinc bromide in sh
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.
