145472-39-5Relevant academic research and scientific papers
The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: Application to the synthesis of (-)-balanol
Unthank, Matthew G.,Hussain, Nigel,Aggarwal, Varinder K.
, p. 7066 - 7069 (2006)
(Chemical Equation Presented) Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reac
An Efficient One-Pot Approach to the Construction of Chiral Nitrogen-Containing Heterocycles under Mild Conditions
Feng, Huan-Xi,Tan, Rui,Liu, Yan-Kai
, p. 3794 - 3797 (2015)
A new, general, and practical procedure for the highly enantioselective synthesis of functionalized nitrogen-containing heterocycles has been developed. The simple cyclic hemiaminals were directly catalyzed for the first time as nucleophiles in an enamine
One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles
Abdul-Rashed, Shukree,Alachouzos, Georgios,Brennessel, William W.,Frontier, Alison J.
supporting information, p. 4350 - 4354 (2020/06/04)
A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven-or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.
A dual arylboronic acid-aminothiourea catalytic system for the asymmetric intramolecular hetero-michael reaction of α,β-unsaturated carboxylic acids
Azuma, Takumi,Murata, Akihiro,Kobayashi, Yusuke,Inokuma, Tsubasa,Takemoto, Yoshiji
supporting information, p. 4256 - 4259 (2014/10/15)
A bifunctional aminoboronic acid has been used to facilitate for the first time the intramolecular aza- and oxa-Michael reactions of α,β- unsaturated carboxylic acids. The combination of an arylboronic acid with a chiral aminothiourea allowed for these re
Triflic acid-mediated phenylation of N-acylaminoalkyl diethylacetals and N-acyl-2-phenyl cyclic amides
King, Frank D.,Caddick, Stephen
, p. 4361 - 4366 (2011/07/29)
The reaction of N-acylaminoalkyl diethylacetals with triflic acid in benzene gave N-acylamino-diphenylalkyls. The proposed intermediates are the N-acyl-2-phenyl cyclic amides, which themselves are similarly converted to N-acylamino-diphenylalkyls.
Rhodium-catalyzed asymmetric hydroformylation of n-allvlamides: Highly enantioselective approach to β2-amino aldehydes
Zhang, Xiaowei,Cao, Bonan,Yu, Shichao,Zhang, Xumu
supporting information; experimental part, p. 4047 - 4050 (2010/08/07)
(Figure Presented) You're having a lahf I The asymmetric hydroformylation (AHF) of allylic compounds, catalyzed by a rhodium-yanphos complex, is a direct and concise route to ss2-amino aldehydes, acids, and alcohols with excellent enantioselectivity (see scheme; TON =turnover number, acac = acetylacetonate).
Single bifunctional ruthenium catalyst for one-pot cyclization and hydration giving functionalized indoles and benzofurans
Nair, Reji N.,Lee, Paul J.,Rheingold, Arnold L.,Grotjahn, Douglas B.
supporting information; experimental part, p. 7992 - 7995 (2010/09/18)
Chemical equation Presented Bifunctional is more than twice as fun! At low loading, catalyst 1 (see scheme) can form two important heterocycle classes, apparently by attack of XH on a vinylidene intermediate. Aza- and nitroindoles can be formed, and all N-protecting groups tested (alkyl, allyl, sulfonyl) were tolerated. The newly formed ring can be deuterated in one step, and for substrates with two terminal alkynes, cyclization can be followed by hydration, making this catalyst uniquely versatile.
Synthesis of alkaloid analogues from β-amino alcohols by β-fragmentation of primary alkoxyl radicals
Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo,Montoya, Adriana,Suarez, Ernesto
, p. 325 - 334 (2007/10/03)
The fragmentation of primary alkoxyl radicals is usually a minor process with respect to hydrogen abstraction and other competing reactions. However, when β-amino alcohols were used as substrates, the scission proceeded in good to excellent yields and no side reactions were observed. The fragmentation can be coupled with an allylation or alkylation reaction, to give alkaloid analogues and functionalized nitrogen heterocycles. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Hemiaminals as substrates for sulfur ylides: Direct asymmetric syntheses of functionalised pyrrolidines and piperidines
Kokotos, Christoforos G.,Aggarwal, Varinder K.
, p. 2156 - 2158 (2008/03/14)
Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enantioselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf. The Royal Society of Chemistry 2006.
Tandem hydroformylation-hydrazone formation-Fischer indole synthesis: A novel approach to tryptamides
Schmidt, Axel M.,Eilbracht, Peter
, p. 2333 - 2343 (2007/10/03)
A novel one-pot synthesis of indole systems via tandem hydroformylation-hydrazone formation-Fischer indolization starting from allylic amides and aryl hydrazines is described. This tandem procedure directly leads to biologically interesting tryptamides and analogues. The Royal Society of Chemistry 2005.
