502685-01-0Relevant articles and documents
Reinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation
Denmark, Scott E.,Carson, Nessa
supporting information, p. 5728 - 5731 (2015/12/11)
Attempts to reproduce eight, putative, enantioselective dibromination and chlorohydroxylation reactions from oft-cited literature studies are described. The reactions were performed with full fidelity to the original report wherever possible. Analysis of the enantiomeric composition was performed by chiral stationary phase HPLC or SFC (CSP-HPLC or CSP-SFC), as opposed to the original report, which used chiral shift reagent NMR spectroscopy. After careful study, the reported levels of enantioselectivity were found to be incorrect. Possible explanations for the false positive results are discussed.
Efficient synthesis of propargylic ethers under the DBU conditions and its application to natural products synthesis
Yokoyama, Tadashi,Kutsumura, Noriki,Ohgiya, Tadaaki,Nishiyama, Shigeru
, p. 578 - 582 (2008/02/11)
Conversion of dibromides carrying O-functional groups at adjacent positions to the corresponding propargylic ethers was successfully carried out under the DBU conditions through 2-bromo-1-alkenes as intermediates. The optically active γ-lactone-class natural products, such as (-)-muricatacin (4) and (R,R)-sapinofuranone B (5) were synthesized using the propargylic ether intermediate produced by the elimination reaction mentioned above.
