7381-98-8Relevant academic research and scientific papers
Cyclopropane-alkene metathesis by gold(i)-catalyzed decarbenation of persistent cyclopropanes
Mato, Mauro,Martín-Torres, Inmaculada,Herlé, Bart,Echavarren, Antonio M.
, p. 4216 - 4219 (2019/05/06)
A gold(i)-catalyzed cyclopropane-alkene metathesis has been demonstrated with two new families of cyclopropane derivatives of naphthalene and phenanthrene (benzo-fused norcaradienes). In this process, metal carbene units are transferred from a persistent
Carboxylates as Nucleophiles in the Enantioselective Ring-Opening of Formylcyclopropanes under Iminium Ion Catalysis
Díaz, Estibaliz,Reyes, Efraim,Uria, Uxue,Carrillo, Luisa,Tejero, Tomas,Merino, Pedro,Vicario, Jose L.
supporting information, p. 8764 - 8768 (2018/05/30)
In this work, carboxylic acids, which are typically regarded as poor nucleophiles, are demonstrated to be competent reagents to promote the ring-opening of formylcyclopropanes after activation of the latter through iminium ion formation. Under optimized r
Diastereoselective borocyclopropanation of allylic ethers using a boromethylzinc carbenoid
Benoit, Guillaume,Charette, André B.
, p. 1364 - 1367 (2017/02/10)
A borocyclopropanation of (E)- and (Z)-allylic ethers and styrene derivatives via the Simmons-Smith reaction using a novel boromethylzinc carbenoid is described. The carbenoid precursor is prepared via a 3-step sequence from inexpensive and commercially available starting materials. This methodology allows for the preparation of 1,2,3-substituted borocyclopropanes in high yields and diastereoselectivities. Several postfunction-alization reactions were also performed to illustrate the versatility of these building blocks.
Spin-selective generation of triplet nitrenes: Olefin aziridination through visible-light photosensitization of azidoformates
Scholz, Spencer O.,Farney, Elliot P.,Kim, Sangyun,Bates, Desiree M.,Yoon, Tehshik P.
, p. 2239 - 2242 (2016/02/18)
Azidoformates are interesting potential nitrene precursors, but their direct photochemical activation can result in competitive formation of aziridination and allylic amination products. Herein, we show that visible-light-activated transition-metal comple
Improved zinc-catalyzed simmons-smith reaction: Access to various 1,2,3-trisubstituted cyclopropanes
Levesque, Eric,Goudreau, Sebastien R.,Charette, Andre B.
supporting information, p. 1490 - 1493 (2014/04/03)
The Simmons-Smith reaction of zinc carbenoids with alkenes is a powerful method to access cyclopropanes containing various substitution patterns. This work exploits the high reactivity of aryldiazomethanes toward zinc halides to generate aryl-substituted carbenoids catalytically. These carbenoids are able to cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates such as styrenes. The zinc catalyst can be modified to tolerate the use of free allylic alcohols.
Enantioselective synthesis of 1,2,3-trisubstituted cyclopropanes using gem-dizinc reagents
Zimmer, Lucie E.,Charette, Andre B.
supporting information; experimental part, p. 15624 - 15626 (2010/01/30)
(Chemical Equation Presented) The first asymmetric cyclopropanation of allylic alcohols using gem-dizinc carbenoids, which allows the synthesis of 1,2,3-substituted cyclopropane derivatives in high yields and excellent enantio- and diastereoselectivities,
In situ generation of zinc carbenoids from diazo compounds and zinc salts: Asymmetric synthesis of 1,2,3-substituted cyclopropanes
Goudreau, Sebastien R.,Charette, Andre B.
supporting information; experimental part, p. 15633 - 15635 (2010/01/29)
(Chemical Equation Presented) The first enantioselective cyclopropanation of alkenes using zinc carbenoids generated in situ from diazo compounds and zinc salts is reported. This new method allows the highly enantioand diastereoselective synthesis of 1,2,
Chemical hermaphroditism: The potential of the Cr(CO)3 moiety to stabilize transition states and intermediates with anionic, cationic, or radical character at the benzylic position
Merlic, Craig A.,Walsh, Joseph C.,Tantillo, Dean J.,Houk
, p. 3596 - 3606 (2007/10/03)
It is known that both benzylic cations and anions are stabilized by Cr(CO)3 complexation. This unusual characteristic of chromium arenes has been the subject of many synthetic, spectroscopic, and physical organic studies over the last four decades. The ef
SYNTHESIS OF STEREOISOMERIC 1-HYDROXYMETHYL-2,3-DIALKYL(DIPHENYL)CYCLOPROPANES AND 1-FORMYL-2,3-DIALKYL(DIPHENYL)CYCLOPROPANES
Komendantov, M.I.,Panasyuk, T.B.
, p. 1308 - 1312 (2007/10/02)
Lithium aluminum hydride reduction of stereoisomeric 2,3-dipropyl(diphenyl)cyclopropanecarboxylic acid esters results in the formation of stereoisomeric 1-hydroxymethyl-2,3-dipropyl(diphenyl)cyclopropanes, which can be oxidized to the corresponding stereo
