16538-47-9Relevant academic research and scientific papers
Dicyclohexylborane-catalyzed hydroboration of 1-halo-1-alkynes with 9-borabicyclo[3.3.1]nonane
Hoshi, Masayuki,Arase, Akira
, p. 567 - 572 (1997)
A catalytic amount of dicyclohexylborane accelerates the hydroboration of 1-halo-1-alkyne (1) with 9-BBN to provide B-[(Z)-1-halo-1-alkenyl]-9-BBN (2) regio- and stereo-selectively.
Preparation and synthetic transformation of alkenyl carbamates into vinyl zirconocene derivatives
Chechik-Lankin, Helena,Marek, Ilan
, p. 3311 - 3318 (2005)
The carbocupration reaction of alkynyl carbamates leads to the stereospecific preparation of polysubstituted alkenyl carbamates. Subsequent treatment of these enol carbamates with the Negishi reagent gave the corresponding vinyl zirconocene species. Georg Thieme Verlag Stuttgart.
Addition of mixed (Alkenyl)dialkylzincates to vicinal diketo esters
Selter, Lars,Harms, Klaus,Koert, Ulrich
supporting information, p. 1215 - 1230 (2017/12/07)
Methods for the regioselective alkylation, arylation, and alkenylation of α,β-diketo esters using organozinc reagents are reported. Alkylation and arylation at the α-position is possi-ble using diorganozinc compounds. Alkenylation can be achieved using mixed (alkenyl)dineopentylzincates.
First total synthesis of Debilisone C
Saikia, Bishwajit,Joymati Devi, Thongam,Barua, Nabin C.
, p. 905 - 913 (2013/03/14)
Total synthesis of Debilisone C, a lactone containing conjugated endiyne has been achieved. The adopted strategy involves the stereoselective construction of the five membered lactone ring and the C20 endiyne chain followed by regioselective coupling of both the parts. The lactone was obtained from the oxidative cleavage of the hydroxy olefin which was derived from the benzyl protected S-epichlorohydrine by regioselective epoxide opening with allyl trimethyl silane in presence of a Lewis acid at -78 °C. Takai olefination, Pd0/Ag1 catalyzed cross-coupling reaction and selective substitution of trimethylsilyl groups were successfully utilized to establish the C20 polyyne chain. The final coupling of both the parts have been carried out by alkyl coupling using LDA in THF-DMPU (1 : 1).
Reactions of perfluorinated alkenyl-, alkynyl-, alkyltrifluoroborates, and selected hydrocarbon analogues with the halogenating agents Hal2 (Hal = F, Cl, Br), "brF" (BrF3-Br2 1:1), and ICl
Bardin, Vadim V.,Adonin, Nicolay Yu.,Frohn, Hermann-Josef
experimental part, p. 565 - 579 (2012/05/20)
Reactions of [Bu4N][RBF3] [R = CnF 2n+1CF=CF (cis, trans), CF2=CF, CF2=C(CF 3), trans-C4H9CF=CF, trans-C6H 5CF=CF, C4H9CH=CH (cis, trans), CF 3C≡C, and C4H9C≡C] with chlorine, bromine, BrF3 + Br2 (as equivalent of "BrF"), and ICl in solution (CH2Cl2, CHCl3, CF 3CH2CF2CH3) led to 1, 2-addition of halogen and/or replacement of boron by halogen (halodeboration). The reaction of [Bu4N][CF3C≡CBF3] with less than equimolar amounts of diluted fluorine (5 %) in 1, 1, 1, 3, 3-pentafluorobutane (PFB) showed only [Bu4N][CF3CF2CF 2BF3] as fluorine addition product besides extensive fluorodeboration. Suspensions of the insoluble K[CF2=CFBF 3] salt reacted with Cl2 and Br2 in CH 2Cl2 giving preferentially products of halogen addition across the C=C bond. In reactions with ICl iododeboration with formation of CF2=CFI occurred besides 1, 2-addition with formation of [CF 2I-CFClBF3]-. The halodeboration reaction of[Bu4N][trans-C4H9CF=CFBF3] with Br2, "BrF", and ICl, of K[trans-C6H 5CF=CFBF3] with Br2, and of [Bu 4N][trans-C4F9CF=CFBF3] with ICl proceeded stereospecifically. Copyright
One-pot synthesis of telluroketene acetals and haloketene acetals using sp2 geminated hetero organobismetallic intermediates
Guerrero Jr., Palimécio G.,De Oliveira, Paulo R.,Baroni, Adriano C.M.,Marques, Francisco A.,Labes, Ricardo,Dabdoub, Miguel J.
experimental part, p. 1582 - 1586 (2012/04/10)
A novel one-pot synthesis of 1,1-dihalo-1-alkenes and 1,1-bis(butyltelluro) -1-alkenes was developed from hydrozirconation of alkynylzinc bromide with Cp2Zr(H)Cl and subsequent capture of the Zn/Zr 1,1-heterodimetallo-1- alkene intermediates wi
Iododesilylation of TIPS-, TBDPS-, and TBS-substituted alkenes in connection with the synthesis of amphidinolides B/D
Sidera, Mireia,Costa, Anna M.,Vilarrasa, Jaume
, p. 4934 - 4937 (2011/11/29)
The C-Si bonds of triisopropylsilyl-substituted alkenes, 1,3-dienes, and related multifunctional substrates, as well as analogous C-TBDPS and C-TBS bonds, are readily and chemoselectively cleaved with NIS (or other sources of I+, such as N-iodo
Total synthesis of clathculins A and B
Hoye, Rebecca C.,Anderson, Gretchen L.,Brown, Susan G.,Schultz, Erica E.
scheme or table, p. 7400 - 7403 (2011/02/22)
Clathculins A and B represent a new class of vic-diamine alkaloids containing a PA2 unit as the basic structure. We report the first total syntheses of 1 and 2, which confirm the assigned structure of each. Dependence of their NMR spectroscopic behavior a
Transfer of alk-1-enyl group from boron to tin: A highly stereoselective synthesis of (E)-alk-1-enyltributylstannanes
Hoshi, Masayuki,Hayatsu, Takaki,Okimoto, Mitsuhiro,Kodama, Satoshi
scheme or table, p. 2945 - 2948 (2010/02/28)
Treatment of (E)-alk-1-enyldicyclohexylboranes with tributyltin methoxide in the presence of galvinoxyl (1 mol%) at room temperature results in transfer of the alk-1-enyl group from boron to tin to give (E)-alk-1- enyltributylstannanes in a highly stereoselective fashion. Subsequent halodestannylation of (E)-alk-1-enyltributylstannanes is allowed to proceed in a one-pot manner to produce the corresponding (E)-1-iodoalk-1-enes and (E)-1-bromoalk-1-enes in good to high yields, respectively. Georg Thieme Verlag Stuttgart.
Modular approach to the synthesis of unsaturated 1-monoacyl glycerols
Coleman, Bridgett E.,Cwynar, Valerie,Hart, David J.,Havas, Fabien,Jakkam, Madan Mohan,Patterson, Suzanne,Ridenour, Sam,Schmidt, Michael,Smith, Eboney,Wells, Angela J.
, p. 1339 - 1342 (2007/10/03)
A modular synthesis of unsaturated 1-monoacylglycerols (1) from cis-1-iodo-1-alkenes [cis-RCH=CHI] and unsaturated carboxylic acids [CH 2=CH(CH2)nCO2H] is described. The method revolves around a Suzuki coupling to establish olefin geometry.
