187814-85-3Relevant academic research and scientific papers
Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C?C Bond Formation
Shimogaki, Mio,Fujita, Morifumi,Sugimura, Takashi
supporting information, p. 15797 - 15801 (2016/12/16)
The enantioselective oxyarylation of (E)-6-aryl-1-silyloxylhex-3-ene was achieved using a lactate-based chiral hypervalent iodine(III) reagent in the presence of boron trifluoride diethyl etherate. The silyl ether promotes the oxidative cyclization, and enhances the enantioselectivity. In addition, the corresponding aminoarylation was achieved.
Tandem Prins/friedel-crafts cyclization for stereoselective synthesis of heterotricyclic systems
Reddy, B.V. Subba,Borkar, Prashant,Yadav,Sridhar,Gree, Rene
, p. 7677 - 7690 (2011/12/02)
Homoallylic substrates such as (E)-6-arylhex-3-enyl alcohols, N-tosylamides, and thiols undergo smooth cross-coupling with various aldehydes in the presence of 10 mol % Sc(OTf)3 and 30 mol % TsOH to afford the trans-fused hexahydro-1H-benzo [f]isochromenes, N-tosyloctahydrobenzo [f] -isoquinolines, and hexahydro-lH-benzo [f]isothiochromenes, respectively. However, the cross-coupling of (Z)-olefins such as 6-arylhex-3-enyl alcohols, N-tosylamides, and thiols with aldehydes affords the corresponding hexahydro-1H-benzo-[f]isochromenes, N-tosyloctahydrobenzo [f]isoquinolines, and hexahydro-1H-benzo[f] isothiochromenes with complete cis selectivity via intramolecular Prins-, aza-Prins-, and thia-Prins/(Figure presented) Friedel - Crafts cyclizations, respectively. Though the Prins cyclization proceeds smoothly under the influence of Sc(OTf)3, high conversions and enhanced reaction rates are achieved using a mixture of Sc(OTf)3 and TsOH (1:3).
