352296-86-7Relevant articles and documents
Transition-Metal-Free Synthesis of Borylated Thiophenes via Formal Thioboration
Bel Abed, Hassen,Blum, Suzanne A.
supporting information, p. 6673 - 6677 (2018/10/24)
A simple, regiocontrolled, and transition-metal-free approach to access exclusively 3-borylated thiophene derivatives is reported. The commercially available B-chlorocatecholborane reagent (ClBcat) acts as a carbophilic Lewis acid to activate the alkyne i
From highly enantioselective catalytic reaction of 1,3-diynes with aldehydes to facile asymmetric synthesis of polycyclic compounds
Turlington, Mark,Du, Yuhao,Ostrum, Samuel G.,Santosh, Vishaka,Wren, Kathryne,Lin, Tony,Sabat, Michal,Pu, Lin
supporting information; experimental part, p. 11780 - 11794 (2011/09/16)
(S)-1,1′-Binaphth-2-ol (BINOL) in combination with ZnEt2, Ti(OiPr)4, and biscyclohexylamine was found to catalyze the highly enantioselective (83-95% ee) addition of various 1,3-diynes to aldehydes of diverse structures. This method provides a convenient pathway to generate a number of optically active dienediynes as the acyclic precursors to polycyclic compounds. The chiral dienediynes undergo highly chemoselective Pauson-Khand (PK) cycloaddition in benzaldehyde by using [Rh(cod)Cl]2 as the catalyst in the presence of rac-BINAP. High diastereoselectivity (up to >20:1) has also been achieved with the chiral dienediyne substrates containing a bulky substituent adjacent to the chiral center. In the presence of the Grubbs II catalyst, ring-closing enyne metathesis of the PK cycloaddition products led to the formation of the desired 5,5,7- and 5,5,8-fused tricyclic compounds. Further highly diastereoselective Diels-Alder reaction of a 5,5,7-tricyclic compound with maleic anhydride produced a 5,5,7,6-polycyclic product. The asymmetric synthesis of polycyclic compounds from optically active dienediynes has established a novel and efficient synthetic route to the structural framework of many biologically significant molecules.
Synthesis of (Z)-1-phenylseleno-1,4-diorganyl-1-buten-3-ynes: Hydroselenation of symmetrical and unsymmetrical 1,4-diorganyl-1,3-butadiynes
Dabdoub, Miguel J.,Baroni, Adriano C.M.,Lenard?o, Eder J.,Gianeti, Thiago R.,Hurtado, Gabriela R.
, p. 4271 - 4276 (2007/10/03)
The hydroselenation of 1-organyl-1,3-butadiynes and 1,4-diorganyl-1,3-butadiynes with the sodium phenylselenolate anion, which was generated in situ by reacting diphenyl diselenide with NaBH4 in aqueous ethanol, results in the regio-, stereo- and chemoselective formation the 1-phenylseleno-4-organyl-1-buten-3-ynes and 1-phenylseleno-1,4-diorganyl-1-buten-3-ynes of Z configuration respectively. The lack of selectivity with the 2-hydroxy-2-methyl-3,5-dodecadiyne was observed and the obtained product structures were studied in detail.
