174858-25-4Relevant academic research and scientific papers
Baylis-Hillman acetates in carbocyclic synthesis: A convenient protocol for synthesis of densely substituted indenes
Basavaiah, Deevi,Reddy, Bhavanam Sekhara,Lingam, Harathi
, p. 1994 - 2003 (2013/03/13)
A simple and facile strategy for synthesis of densely substituted indenes have been developed from Baylis-Hillman acetates in a two step protocol, that is, (1) via treatment with DABCO and then reaction with alkyl 3-oxobutanoates in the presence of K2CO3 (2) followed by the intramolecular Friedel-Crafts cyclization of the resulting keto-diesters using titanium tetrachloride.
Triphosgene mediated chlorination of Baylis-Hillman adducts
Thatikonda, Narender Reddy,Chebolu, Naga Sesha Sai Pavan Kumar,Budde, Mahendar,Vaidya, Jayathirtha Rao
, p. 513 - 519 (2012/07/30)
An efficient method for the preparation of allyl chlorides from Baylis-Hillman adducts has been developed using triphosgene/pyridine system. This method is best illustrated by its advantages like operational simplicity, excellent yields, short reaction ti
On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering
Brenna, Elisabetta,Fronza, Giovanni,Fuganti, Claudio,Gatti, Francesco G.,Manfredi, Alessia,Parmeggiani, Fabio,Ronchi, Paolo
, p. 94 - 101 (2012/10/30)
The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes, as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction.
A simple and efficient protocol for chlorination of baylis-hillman adducts using PPh3/CCl4
Das, Biswanath,Kanth, Boddu Shashi,Reddy, Kongara Ravinder,Satyalakshmi, Gandham,Kumar, Rathod Aravind
, p. 512 - 513 (2008/09/21)
PPh3/CCl4 system has been employed for the stereoselective synthesis of (Z)- and (E)-allyl chlorides from Baylis-Hillman adducts in excellent yields. Copyright
Syntheses of (Z)-allyl chlorides from Baylis-Hillman adducts with a trichlorotriazine/DMF system
Li, Jian,Li, Shaoyu,Jia, Xueshun,Zhang, Yongmin
, p. 48 - 49 (2008/09/20)
Stereoselective transformation of Baylis-Hillman adducts 1 into corresponding (2)-allyl chlorides 2 have been achieved by treatment with 2,4,6-trichloro [1,3,5]triazine and N, N-dimethyl formamide. This novel approach proceeds readily at room temperature
First asymmetric synthesis of a C2-symmetric 2-endo,6-endo-disubstituted bispidine
Breuning, Matthias,Hein, David
, p. 1410 - 1418 (2008/02/09)
The enantioselective synthesis of a C2-symmetric 2-endo,6-endo-disubstituted bispidine (3,7-diazabicyclo[3.3.1]nonane) has been accomplished for the first time. The key step was a Michael addition of the protected β-amino ester methyl (R)-3-{N-
A mild and efficient method for chlorination of Baylis-Hillman adducts using PPh3/Cl3CCONH2
Das, Biswanath,Chowdhury, Nikhil,Damodar, Kongara,Ravikanth, Bommena
, p. 2037 - 2040 (2008/03/13)
A new and convenient stereoselective synthesis of (Z)-2-(chloromethyl)alk- 2-enoates has been achieved from Baylis - Hillman adducts by treatment with PPh3/Cl3CCONH2 at room temperature. The synthesis can proceed under mil
Silica chloride-catalyzed one-pot isomerizationchlorination, arylation, and etherification of BaylisHillman adducts
Shanmugam, Ponnusamy,Viswambharan, Baby,Vaithiyanathan, Vadivel
, p. 850 - 856 (2008/03/12)
A convenient and efficient one-pot isomerization?chlorination, arylation, and etherification of several Baylis?Hillman adducts with silica chloride, an eco-friendly heterogeneous catalyst, silica chloride?arenes, and silica chloride?saturated and unsatura
Highly efficient and stereoselective synthesis of (2Z)-2-(halomethyl)alk-2- enoates in acidic ionic liquid
Ying, Taokei,Bao, Weiliang,Wang, Zhonghua,Zhang, Yongmin
, p. 96 - 98 (2007/10/03)
NaCl, NaBr and Nal immobilised in 1-butyl-3-methylimidazolinium hydrogen sulfate ([bmim][HSO4]) ionic liquid was found to be an efficient halogenation system for the conversion of Baylis-Hillman adducts, 3-hydroxy-2-methylenealkanoates, into (2
