- Direct Access to α,β-Unsaturated Ketones via Rh/MgCl2-Mediated Acylation of Vinylsilanes
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We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized with synthetically useful yield.
- Chen, Zi-Yan,Deng, Xue-Zu,Song, Yang,Xue, Fei,Yamane, Motoki,Yue, Yan-Ni
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p. 12693 - 12704
(2021/09/28)
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- A Copper(I)-Catalyzed Enantioselective γ-Boryl Substitution of Trifluoromethyl-Substituted Alkenes: Synthesis of Enantioenriched γ,γ-gem-Difluoroallylboronates
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The first catalytic enantioselective γ-boryl substitution of CF3-substituted alkenes is reported. A series of CF3-substituted alkenes was treated with a diboron reagent in the presence of a copper(I)/Josiphos catalyst to afford the c
- Kojima, Ryoto,Akiyama, Sota,Ito, Hajime
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supporting information
p. 7196 - 7199
(2018/06/15)
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- Stereodivergent Olefination of Enantioenriched Boronic Esters
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A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.
- Armstrong, Roly J.,García-Ruiz, Cristina,Myers, Eddie L.,Aggarwal, Varinder K.
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supporting information
p. 786 - 790
(2017/01/14)
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- An expeditious and atom-economical synthesis of a new generation of substituted [4.6.4.6]fenestradienes
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With finesse and strain: Highly strained derivatives of fenestranes, [4.6.4.6]fenestradienes, have been prepared using a remarkable reaction cascade featuring a 4-exo-dig cyclocarbopalladation, a Sonogashira-type coupling, a regioselective alkynylation, and an 8π/6π electrocyclization sequence. Copyright
- Charpenay, Melanie,Boudhar, Aicha,Blond, Gaelle,Suffert, Jean
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supporting information; experimental part
p. 4379 - 4382
(2012/06/29)
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- Palladium-catalyzed direct functionalization of benzoxazoles with alkenyl iodides
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A straightforward procedure for the palladium-catalyzed direct functionalization of benzoxazoles with alkenyl iodides is described. The reactions employ a Pd(II)-precatalyst and use 'on water' conditions to achieve the ready union of a range of di- and tr
- Gerelle, Maria,Dalencon, Anne J.,Willis, Michael C.
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supporting information; experimental part
p. 1954 - 1957
(2012/05/07)
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- Iododesilylation of TIPS-, TBDPS-, and TBS-substituted alkenes in connection with the synthesis of amphidinolides B/D
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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
- Sidera, Mireia,Costa, Anna M.,Vilarrasa, Jaume
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p. 4934 - 4937
(2011/11/29)
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- Catalytic enantioselective conjugate allylation of unsaturated methylidene ketones
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The use of unsaturated methylidene ketones in catalytic conjugate allylations allows a significant expansion in substrate scope and, with appropriate chiral ligands, occurs in a highly enantioselective fashion.(Figure Presented)
- Brozek, Laura A.,Sieber, Joshua D.,Morken, James P.
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supporting information; scheme or table
p. 995 - 997
(2011/05/15)
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- Synthesis of aminocyclobutanes through ring expansion of N-vinyl-β-lactams
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Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane- containing δ-lactams can be accessed from N-vinyl-β-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lact
- Cheung, Lawrence L. W.,Yudin, Andrei K.
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supporting information; body text
p. 1281 - 1284
(2009/08/12)
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- A practical transformation of aldehydes into (E)-iodoalkenes with geminal dichromium reagents
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A catalytic cycle of a chromium salt in a stereoselective transformation of aldehydes to (E)-l-iodoalkenes using a geminal dichromium reagent, is assembled with zinc, Me3SiCl, and NaI in dioxane.
- Takai, Kazuhiko,Ichiguchi, Tetsuya,Hikasa, Shintaro
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p. 1268 - 1270
(2007/10/03)
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- Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes
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A practical synthesis of (E)-1-stannylalk-1-enes containing a range of oxygen and nitrogen functionality is highlighted, involving hydrostannylation followed by palladium-catalysed carbon-bromine bond cleavage reactions of 1-bromoalkynes.
- Boden, Christopher D. J.,Pattenden, Gerald,Ye, Tao
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p. 2417 - 2419
(2007/10/03)
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