Satoshi Minakata

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTOrganic Reactions on Silica in WaterSatoshi Minakata* and Mitsuo KomatsuView Author Information Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan* Author to whom correspondence should be addressed (e-mail [email protected]).Cite this: Chem. Rev. 2009, 109, 2, 711–724Publication Date (Web):December 10, 2008Publication History Received30 May 2008Published online10 December 2008Pu

tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cycloaddition of oximes and alkenes/alkynes, leading to the formation of a variety of isoxazolines or isoxazoles under mild conditions.

Nitrogen-containing heterocycles--such as aziridines, pyrrolidines, piperidines, and oxazolines--frequently show up as substructures in natural products. In addition, some of these species show potent biological activities. Therefore, researchers would like to develop practical and convenient methods for constructing these heterocycles. Among the available methods, the transfer of N(1) units to organic molecules, especially olefins, is a versatile method for the synthesis of N-heterocycles. This

The addition of pyridine N-oxide is necessary to obtain high enantioselectivities in the asymmetric aziridination of styrene derivatives through transfer of a nitrogen atom from chiral, toluenesulfonic anhydride activated nitridomanganese complex 1 [Eq. (a)]. Remarkably, high stereospecificity was observed in all the aziridinations of trans- and cis-1,2-disubstituted alkenes. R¹ =H, Me, nPr, iPr; R² =H, Me; Ts=p-toluenesulfonyl.

Hold on tight! Reaction of CO2 with unsaturated alcohols and tBuOI to form cyclic carbonates leads to fixation of the greenhouse gas. In contrast to known CO2 fixation methods, this process proceeds under extremely mild conditions. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the c

It's all the hype: An oxidative dimerization reaction of aromatic amines utilizing tert-butyl hypoiodite (tBuOI) under mild reaction conditions leads to aromatic azo compounds (see scheme). The method allows access to unsymmetric aromatic azo compounds, which are difficult to prepare by conventional synthetic methods, in a selective manner.

[Structure: see text] tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cyclization of N-alkenylamides leading to a variety of N-heterocycles under extremely mild conditions. When N-alkenylsulfonamides were employed in the reaction, three- to six-membered saturated N-heterocycles were obtained in good to excellent yields with complete stereoselectivity. The method was applicable to the cyclization of alkenylbenzamide derivatives to afford N-, O- or N-, S-heterocycles.

Olefins can be converted into aziridines by using a chloramine-T/I2 system, and silica and water as the reaction medium (see picture). Moreover, the ring-opening reaction of the resulting aziridine with an azide or a cyanide ion proceeds in the same medium. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z52842_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any support

A new synthetic procedure for the aminochlorination of olefins for the synthesis of vicinal chloroamine derivatives using a combination of Chloramine-T and carbon dioxide is described. The method can be applied to a variety of olefins, including an electron-sufficient olefin and a conjugated diene.

A palladium catalyzed regioselective borylative ring opening reaction of 2-arylaziridines to give β-amino-β-arylethylborates was developed. The reaction reported herein represents the first example of ring-opening borylation of non-vinylic aziridines and direct borylative C(sp³)-N bond cleavage of neutral organic substrates. NMR studies and density functional theory (DFT) calculations suggested that the active intermediate for the reaction is a PdL₂ complex [L = P(<i>t</i>-

The ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N',N'-tetramethylethylenediamine, led to the production of beta-functionalized sulfonamides in good to excellent yields with high regioselectivity. [reaction: see text]

tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for synthesis of aziridines from olefins and sulfonamides. The aziridination of olefins was achieved by using sulfonamides with t-BuOI. Our preliminary findings represent the example of metal-free aziridination of olefins with readily accessible sulfonamides as a nitrogen source.

A new and simple method for the synthesis of oxazolines from readily accessible olefins and amides using tert-butyl hypoiodite is described; aromatic/aliphatic olefins and amides can be used in the reaction to give a variety of oxazolines.

Hypervalent iodine(III)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes under metal-free conditions has been developed. The reaction allows for direct access to quinoxalines bearing two electron-withdrawing groups in an efficient manner.

The stereospecific, substrate (nitrogen source)-controlled intermolecular <i>anti</i>- and <i>syn</i>-1,2-diaminations of unactivated alkenes using the same catalysis (an iodine catalyst) is reported. The combined use of the two potential methods provides access to all of the disastereomeric forms of 1,2-diamines in spite of the availability of <i>E</i>- and <i>Z</i>-alkenes, and the resulting products can be readily converted into free vicinal diamines.