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- W2011109966 abstract "A new efficient synthetic route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines that relies on copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols under mild and operationally straightforward conditions is described. For reactions leading to the trans-2,5-dihydro-1H-pyrrole product, yields of 52–83% along with trans selectivities up to >99:1 dr and ee values up to 97% were accomplished from enantioenriched 1-(tosylamino)pent-4-en-2-ols ranging from 91–99% ee. Without the need for inert and moisture-free conditions, reactions involving 1-[2- (tosylamino)phenyl]but-3-en-1-ols afforded the corresponding 1,2-dihydroquinoline products in excellent yields up to 99% and with complete chemoselectivity. The mechanism is suggested to involve cop- per(II)-mediated dehydration of the homoallylic amino alcohol. Protonation of the resultant cop- per(II)-activated aminodiene is then thought to trigger subsequent intramolecular hydroamination to give the partially hydrogenated nitrogen heterocycle." @default.
- W2011109966 created "2016-06-24" @default.
- W2011109966 creator A5006510965 @default.
- W2011109966 creator A5027691896 @default.
- W2011109966 creator A5039408031 @default.
- W2011109966 creator A5053308903 @default.
- W2011109966 date "2010-09-14" @default.
- W2011109966 modified "2023-10-06" @default.
- W2011109966 title "Copper(II) Triflate-Catalyzed Intramolecular Hydroamination of Homoallylic Amino Alcohols as an Expedient Route to trans-2,5-Dihydro-1H-pyrroles and 1,2-Dihydroquinolines" @default.
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