120809-09-8Relevant academic research and scientific papers
Asymmetric induction in an enammonium-iminium rearrangement. Mechanistic insight via NMR, deuterium labeling, and reaction rate studies. Application to the stereoselective synthesis of pyrroloisoquinoline antidepressants
Sorgi, Kirk L.,Maryanoff, Cynthia A.,McComsey, David F.,Graden, David W.,Maryanoff, Bruce E.
, p. 3567 - 3579 (2007/10/02)
Reductive deoxygenation of 5a, 5b, 7a, or 7b with borane-THF in trifluoroacetic acid yielded a product mixture (6a/6b or 4a/4b) highly biased (90-95%) in favor of the trans diastereomer (6b or 4b). The mechanism of this process was probed by NMR spectrosc
HIGHLY STEREOCONTROLLED PROTON TRANSFER IN AN ENAMMONIUM-IMINIUM REARRANGEMENT. MECHANISM OF THE STEREOSELECTIVE DEOXYGENATION OF 6-ARYL-6-HYDROXY-1,2,3,5,6,10b-HEXAHYDROPYRROLOISOQUINOLINES WITH BORANE-THF IN TRIFLUOROACETIC ACID.
Maryanoff, Bruce E.,McComsey, David F.,Mutter, Martin S.,Sorgi, Kirk L.,Maryanoff, Cynthia A.
, p. 5073 - 5076 (2007/10/02)
Either diastereomer of 2 or 10 is deoxygenated with BH3-THF/CF3CO2H to give mainly the trans product, 3b or 11b.The process involes a key enammonium-iminium rearrangement in which there is almost exclusive proton delivery from a single face.
