733010-51-0Relevant articles and documents
Mild and highly enantioselective vinylogous aldol reaction of brassards diene with aromatic aldehydes by combined lewis acid catalyst
Wang, Guowei,Zhao, Jinfeng,Zhou, Yuhan,Wang, Baomin,Qu, Jingping
supporting information; experimental part, p. 5326 - 5329 (2010/10/19)
(Figure presented) The combined Lewis acid catalytic system, generated from (R)-1,1′-bi-2-naphthol [(R)-BINOL], Ti(O-i-Pr)4, H 2O, and lithium chloride, effectively catalyzed the enantioselective vinylogous aldol reaction of Brassard
A mild and efficient asymmetric hetero-diels-alder reaction of the brassard diene with aldehydes
Fan, Qian,Lin, Lili,Liu, Jie,Huang, Yaozong,Feng, Xiaoming
, p. 3542 - 3552 (2007/10/03)
This paper describes the successful development of the hetero-Diels-Alder (HDA) reaction of the Brassard diene with aldehydes in the presence of a series of titanium(IV) tridentate Schiff-base complexes under mild conditions. The influence of the substituent of the chiral Schiff-base ligands on the enantioselectivities of the reaction was studied. It was found that ligand L13 is a highly enantioselective ligand for the Ti-catalyzed HDA reaction, affording 6-substituted 4-ethoxy-5,6-dihydropyran-2-one in up to 99 % ee. The mechanism of the HDA reaction between the Brassard diene and benzaldehyde in the presence of the (Schiff base)TiIV complex was investigated. The results indicate that the reaction pathway is influenced by reaction temperature: at higher temperature (0°C), the reaction is mostly a Diels-Alder process, whereas at lower temperature (-78°C) it is a Mukaiyama aldol process. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.