58324-90-6Relevant articles and documents
Microwave-assisted Raney nickel reduction of bispidinone thioketals to N,N′-dialkylbispidines
Toom, Lauri,Grennberg, Helena,Gogoll, Adolf
, p. 2064 - 2068 (2007/10/03)
A series of N,N′-dialkyl-3,7-diazabicyclo[3.3.1]nonanes was prepared by microwave-assisted reduction of a common dithiolane precursor with Raney nickel, using the corresponding alkanol as solvent. The method avoids the use of hydrazine. Georg Thieme Verla
Asymmetric Deprotonations: Lithiation of N-(tert-Butoxycarbonyl)indoline with sec-Butyllithium/ (-)-Sparteine
Bertini Gross, Kathleen M.,Jun, Young M.,Beak, Peter
, p. 7679 - 7689 (2007/10/03)
The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.
