PMCC PMCC

Search tips
Search criteria

Advanced
Results 1-4 (4)
 

Clipboard (0)
None

Select a Filter Below

Journals
Authors
more »
Year of Publication
Document Types
1.  Tri-tert-butyl 3-oxo-4-oxa-1,8,11-tri­aza­spiro­[5.6]dodecane-1,8,11-tri­acetate 
The title compound, C26H45N3O8, is a bicyclic mol­ecule; the seven-membered diazepane ring has a twisted-chair conformation and the six-membered morpholine ring has a boat conformation.
doi:10.1107/S0108270109049361
PMCID: PMC2850304  PMID: 20354302
2.  Synthesis of highly enantioenriched 3,4-dihydroquinolin-2-ones by 6-exo-trig radical cyclizations of axially chiral α-halo-ortho-alkenyl anilides 
Journal of the American Chemical Society  2009;131(42):15492-15500.
Radical cyclizations (Bu3SnH, Et3B/air, rt) of racemic α-halo-ortho-alkenyl anilides provide 3,4-dihydroquinolin-2-ones in high yield. Cyclizations of enantioenriched precursors occur in similarly high yields and with transfer of axial chirality to the new stereocenter of the products with exceptionally high fidelity (often > 95%). Single and tandem cyclizations of α-halo-ortho-alkenyl anilides bearing an additional substituent on the α-carbon occur with high chirality transfer and high diastereoselectivity. Straightforward models are proposed to interpret both the chirality transfer and diastereoselectivity aspects. These first examples of an approach for axial chiral transfer from a reactive species in the amide to an acceptor suggest broad potential for extension both within and beyond radical reactions.
doi:10.1021/ja9066282
PMCID: PMC2784126  PMID: 19799432
3.  Synthesis and biological evaluation of the first pentafluorosulfanyl analogs of mefloquine† 
Organic & biomolecular chemistry  2009;7(20):4163-4165.
Two novel SF5 analogs of the antimalarial agent mefloquine were synthesized in 5 steps and 10–23% overall yields and found to have improved activity and selectivity against malaria parasites. This work also represents the first report of SF5-substituted quinolines.
doi:10.1039/b911483a
PMCID: PMC2929370  PMID: 19795052
4.  Fluorous Parallel Synthesis of a Piperazinedione-Fused Tricyclic Compound Library 
A fluorous-linker-assisted solution-phase protocol has been developed and applied to parallel synthesis of a piperazinedione-fused tricyclic compound library. The one-pot [3 + 2] cycloaddition of fluorous amino esters, aldehydes, and maleimides afforded bicyclic proline derivatives. The intermediates were subjected to N-acylation with chloroacetyl chloride, followed by displacement reactions with amines. Linker cleavage with concomitant lactamization yielded the final products. Microwave heating was employed to facilitate several reaction steps and fluorous solid phase extraction (F-SPE) was employed to purify the intermediates. During the method development, a small library containing sixteen analogs was prepared. The optimized conditions were applied to the synthesis of a production library containing ninety analogs.
doi:10.1021/cc900003q
PMCID: PMC2921976  PMID: 19301852

Results 1-4 (4)