Metal-Free Transfer Hydroiodination of C-C Multiple Bonds
The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.
Chen, Weiqiang,Walker, Johannes C. L.,Oestreich, Martin
supporting information
p. 1135 - 1140
(2019/01/11)
A bismuth(III)-catalyzed friedel-crafts cyclization and stereocontrolled organocatalytic approach to (-)-platensimycin
A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)3 to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promoted cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.
Eey, Stanley T.-C.,Lear, Martin J.
supporting information; experimental part
p. 5510 - 5513
(2011/03/18)
Studies on the synthesis of apoptolidin A. 1. Synthesis of the C(1)-C(11) fragment
(Chemical Equation Presented) A synthesis of the C(1)-C(11) fragment of apoptolidin A has been accomplished by a convergent route involving the stereoselective glycosidation of 9 and the Suzuki cross-coupling reaction of bromodienoate 7 and the vinylboran
Handa, Masaki,Scheldt, Karl A.,Bossart, Martin,Zheng, Nan,Roush, William R.
p. 1031 - 1035
(2008/09/18)
From dicarbonylallene to 1-aryl-3,6-dimethyl-4-aminoaryl-2-pyridones: a one-pot versatile and uncatalyzed synthesis
Reaction of amines with an allenic precursor leads to new 1-aryl-3,6-dimethyl-4-aminoaryl-2-pyridones in good yields. These syntheses can be performed in two distinct steps, allowing the possibility to introduce different substituents in the positions 1 a