132816-01-4Relevant articles and documents
1,3-Asymmetric Induction in Diastereoselective Allylations of Chiral N-Tosyl Imines
Fettinger, James C.,Gutierrez, David A.,Lo, Anna,Shaw, Jared T.,Toth-Williams, Garrett
, (2022/02/07)
Lewis acid mediated allylations of β-alkoxy N-tosyl imines using allyltrimethylsilane lead to 3-alkoxy homoallylic N-tosyl amines with anti-selectivity. Two methods of Cu(OTf)2-mediated allylations are reported herein, demonstrating that diastereoselectiv
Enantioselective allyltitanations and metathesis reactions. Application to the synthesis of piperidine alkaloids (+)-sedamine and (-)-prosophylline
Cossy, Janine,Willis, Catherine,Bellosta, Veronique,BouzBouz, Samir
, p. 1982 - 1992 (2007/10/03)
An enantioselective synthesis of the piperidine alkaloids (+)-sedamine and (-)-prosophylline is reported. The synthesis of (+)-sedamine has been achieved in 12 steps with an overall yield of 20% from benzaldehyde, and (-)-prosophylline was obtained in 15 steps with an overall yield of 9.2%, starting from D-glyceraldehyde acetonide 14. The key steps are enantioselective allyltitanation reactions and ring-closing or cross-metathesis reactions.