189031-66-1Relevant academic research and scientific papers
Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E-Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers
Lee, Jihong,Kim, Kyung Hwan,Lee, Ok Suk,Choi, Tae-Lim,Lee, Hee-Seung,Ihee, Hyotcherl,Sohn, Jeong-Hun
, p. 7591 - 7596 (2016/09/09)
As a guide for selective reactions toward either Z- or E-alkene in a metathesis reaction, the relative preference of metathesis Ru catalysts for each stereoisomer was determined by a method using time-dependent fluorescence quenching. We found that Ru-1 p
Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: Facile synthesis of bicyclo[4.1.0]heptan-5-ones
Liu, Bang,Song, Ren-Jie,Ouyang, Xuan-Hui,Li, Yang,Hu, Ming,Li, Jin-Heng
, p. 12819 - 12822 (2015/08/06)
We here describe a new palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes at room temperature using tBuONO as an oxidant for the synthesis of 3-bicyclo[4.1.0]heptan-5-ones. This cascade strategy involves the hydration, cyclization and cycl
Access to cyclobutene-fused azepines through au-catalyzed cycloisomerization of stable alkyne tethered ketene N,N -acetals
Nayak, Sanatan,Ghosh, Nayan,Sahoo, Akhila K.
supporting information, p. 2996 - 2999 (2014/06/23)
A base promoted reaction between N-protected propargyl amines and 3-bromopropiolate readily provides an array of novel stable alkyne-tethered ketene N,N-acetals in good yields. A wide range of structurally complex cyclobutene-fused azepine heterocycles are synthesized through the gold-catalyzed intramolecular cycloisomerization of ketene N,N-acetals for the first time. A plausible reaction pathway is deduced on the basis of the 1H NMR studies.
Ti-catalyzed straightforward synthesis of exocyclic allenes
Munoz-Bascon, Juan,Hernandez-Cervantes, Carmen,Padial, Natalia M.,Alvarez-Corral, Miriam,Rosales, Antonio,Rodriguez-Garcia, Ignacio,Oltra, J. Enrique
supporting information, p. 801 - 810 (2014/01/23)
Exocyclic allenes constitute useful building blocks in organic synthesis and have recently been identified as key intermediates in the synthesis of natural products. Here the first general method for the most straightforward synthesis of exocyclic allenes
Iron(ii)-catalysed [2+2+2] cycloaddition for pyridine ring construction
Richard, Vincent,Ipouck, Melinda,Merel, Delphine S.,Gaillard, Sylvain,Whitby, Richard J.,Witulski, Bernhard,Renaud, Jean-Luc
supporting information, p. 593 - 595 (2014/01/06)
We report a new, simple and air-stable iron(ii) complex pre-catalyst for the synthesis of substituted pyridines via a [2+2+2] cycloaddition between diynes and nitrile derivatives. The Royal Society of Chemistry 2014.
Secondary phosphine oxide-gold(I) complexes and their first application in catalysis
Schroeder, Felix,Tugny, Coralie,Salanouve, Elise,Clavier, Herve,Giordano, Laurent,Moraleda, Delphine,Gimbert, Yves,Mouries-Mansuy, Virginie,Goddard, Jean-Philippe,Fensterbank, Louis
supporting information, p. 4051 - 4056 (2014/10/15)
A series of new secondary phosphine oxide (SPO)-gold(I) complexes have been synthesized and characterized by X-ray crystallography. Complexes exhibited dimeric structures interconnected by O-H···Cl hydrogen bonds. Their first use in homogeneous catalysis
An efficient, overall [4+1] cycloadditon of 1,3-dienes and nitrene precursors
Wu, Qiong,Hu, Jian,Ren, Xinfeng,Zhou, Jianrong
supporting information; experimental part, p. 11553 - 11558 (2011/11/29)
Intermolecular cycloadditions of conjugated dienes and nitrene precursors usually produce aziridines. A generally useful method was lacking to directly provide the [4+1] cycloadducts, 3-pyrrolines. We have realized this transformation by using an uniquely active catalyst, copper(II) 1,1,1,5,5,5-hexafluoroacetylacetonate ([Cu(hfacac)2]). The method is applicable to a wide array of dienes with good yields. When 1,4-disubsituted dienes are used as substrates, good-to-excellent cis or trans selectivity can be obtained. Interestingly, the cis or trans preference depends on the nature of the substituents, rather than diene geometry. Mechanistic studies reveal that the [4+1] cycloaddition proceeds through diene aziridination and subsequent ring expansion. Among common copper catalysts, only [Cu(hfacac)2] can efficiently catalyze both steps, which explains the unique efficiency of the catalyst.
Titanium(IV) chloride-mediated carbocyclization of 1,6-Enynes: Selective synthesis of 3-Azabicyclo[3.1.0]hexanes and functionalized allenes by controlling the reaction temperature
Zhang, Zhen,Shi, Min
, p. 2610 - 2614 (2011/06/28)
1,6-Enynes can be transformed into 3-azabicyclo[3.1.0]hexanes and functionalized allenes in moderate to good yields along with moderate to high diastereoselectivities by controlling the reaction temperature in the presence of titanium(IV) chloride. A plausible mechanism is proposed. 1,6-Enynes can be transformed into 3-azabicyclo[3.1.0]hexanes and functionalized allenes respectively in moderate to goodyields along with moderate to high diastereoselectivities by controlling the reaction temperature in the presence of titanium(IV) chloride. A plausible mechanism is proposed.
Iridium-mediated isomerization-cyclization of bicyclic Pauson-Khand derived allylic alcohols
Kavanagh, Yvonne,Chaney, Ciara M.,Muldoon, Jimmy,Evans, Paul
supporting information; experimental part, p. 8601 - 8604 (2009/04/04)
(Chemical Equation Presented) Treatment of 2-(toluene-4-sulfonyl)-2,3,4,4a, 5,6-hexahydro-1H-[2]pyrindin-6-ol 10, accessed from the diastereoselective Luche reduction of a Pauson-Khand derived bicylic cyclopentenone, with a catalytic amount of (1,5-cycloo
Sequential Ru-Pd catalysis: A two-catalyst one-pot protocol for the synthesis of N- and O-heterocycles
Trost, Barry M.,Machacek, Michelle R.,Faulk, Brian D.
, p. 6745 - 6754 (2007/10/03)
An atom economic, selective, and highly practical two-metal one-pot synthesis of heterocycles has been developed that efficiently affords enantio- and diastereopure N- and O-heterocyclic products. Furthermore, use of a chiral catalyst in the two-metal procedure allows formation of all possible diastereomers, even those that are traditionally difficult to access via cyclization routes due to thermodynamics. Interestingly, the nature of the enantiodiscriminating event differs between the use of amine versus alcohol nucleophiles. The method also affords heterocyclic products that are synthetically useful intermediates. Through the Z-vinylsilane a variety of stereodefined trisubstituted olefin products can be accessed including several all-carbon motifs. Finally, the utility of these heterocyclic products in total synthesis is demonstrated through concise syntheses of a kainoid intermediate, a constituent of oil of rose, and the ring B portion of bryostatin, a potent chemotherapeutic.
