624732-11-2Relevant academic research and scientific papers
Trifluoromethylated amino alcohol as chiral auxiliary for highly diastereoselective and fast Simmons-Smith cyclopropanation of allylic amine
Katagiri, Toshimasa,Iguchi, Naomi,Kawate, Tomomi,Takahashi, Satoshi,Uneyama, Kenji
, p. 1157 - 1160 (2007/10/03)
Three advantages of a trifluoromethylated amino alcohol auxiliary in the Simmons-Smith cyclopropanation of allylic amines are described. The trifluoromethylated amino alcohol auxiliary reduces unwanted side reactions induced by its acidic, and thus less n
Highly Diastereoselective Simmons-Smith Cyclopropanation of Allylic Amines
Aggarwal, Varinder K.,Fang, Guang Yu,Meek, Graham
, p. 4417 - 4420 (2007/10/03)
(Equation presented) Cyclopropanation of allylic tertiary amines using the Simmons-Smith reagent has been achieved by employing chelating groups in close proximity to the amine. The chelating groups promote cyclopropanation at the expense of N-ylide formation. Using pseudoephedrine as the chelating group, high diastereoselectivity is observed.
