397333-58-3Relevant academic research and scientific papers
Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I
Gangadhar, Pamarthi,Ramakrishna, Sayini,Venkateswarlu, Ponneri,Srihari, Pabbaraja
, p. 2313 - 2320 (2018)
The stereoselective total synthesis of strongylodiol H and I has been accomplished. The synthetic procedure comprised the stereoselective reduction of a ketone functionality in an ene–yne–one employing CBS as a catalyst and a Cadiot–Chodkiewicz coupling r
Gold-Catalyzed Intramolecular Tandem Cyclization of Indole-Ynamides: Diastereoselective Synthesis of Spirocyclic Pyrrolidinoindolines
Zheng, Nan,Chang, Yuan-Yuan,Zhang, Li-Jie,Gong, Jian-Xian,Yang, Zhen
supporting information, p. 371 - 375 (2016/05/19)
A gold-catalyzed intramolecular tandem cyclization of indole-ynamide affords tetracyclic spirocyclic pyrrolidinoindoline bearing an all-carbon quaternary stereocentre in a single step; however, when the reaction was carried out in the presence of BF3·Et2O, the corresponding tricyclic spirocyclic pyrrolidinoindoline-based enones are produced through a key 1,5-hydride shift. The developed chemistry provides a diastereoselective and straightforward entry to structurally diverse polycylic pyrrolidinoindolines from indole-ynamides in one-pot reactions under mild conditions.
Stille reactions catalytic in tin: A "Sn-F" route for intermolecular and intramolecular couplings
Gallagher, William P.,Maleczka Jr., Robert E.
, p. 841 - 846 (2007/10/03)
(Chemical Equation Presented) Polymethylhydrosiloxane (PMHS) made hypercoordinate by KF(aq) allows Me3SnH to be recycled during a Pd(0)-catalyzed hydrostannation/Stille cascade. Starting with a variety of alkynes, in situ vinyltin formation is followed by Stille reaction with aryl, styryl, benzyl, or vinyl electrophiles present in the reaction mixture. Both inter- and intramolecular versions of the process are possible with tin loads of approximately 6 mol %. Regeneration of the organotin hydride is believed to proceed through a Me3SnF intermediate. Given the aggregated nature of organotin fluorides and the ability to use these organotins in substoichiometric quantities, the hazards and purification problems associated with the removal of organotin wastes from reaction mixtures are minimized.
Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides
Zhang, Yanshi,Hsung, Richard P.,Tracey, Michael R.,Kurtz, Kimberly C. M.,Vera, Eymi L.
, p. 1151 - 1154 (2007/10/03)
(Equation presented) A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO4·5H2O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.
Stille couplings catalytic in tin: a "Sn-F" approach.
Maleczka Jr.,Gallagher
, p. 4173 - 4176 (2007/10/03)
A new tin recycling method for Stille couplings catalytic in tin is reported. PMHS made hypercoordinate by KF((aq)) allows Me(3)SnH to be efficiently recycled during a Pd(0)-catalyzed hydrostannation/Stille cascade. Relative to previously disclosed protoc
