114106-91-1Relevant articles and documents
Enantioselective Morita–Baylis–Hillman Reaction of Acrylates with Nitrobenzaldehydes Promoted by the Bifunctional Ferrocene-Based Phosphinothiourea Organocatalysts
Li, Chuang,Ma, Peng-Fei,Lei, Yang,Chen, Hui,Guan, Shao-Yu,Jiang, Ru,Chen, Wei-Ping
, p. 1429 - 1434 (2016)
Abstract: A series of ferrocene-based bifunctional phosphinothiourea organocatalysts were synthesized and applied to the enantioselective Morita–Baylis–Hillman reaction of acrylates with nitrobenzaldehydes, giving the desired products in up to 99.7?% ee.
Bifunctional (Thio)urea-Phosphine Organocatalysts Derived from d -Glucose and α-Amino Acids and Their Application to the Enantioselective Morita-Baylis-Hillman Reaction
Gergelitsová,Tauchman,Císa?ová,Vesely
supporting information, p. 2690 - 2696 (2015/11/27)
Novel (thio)urea-tertiary phosphines were developed for use as bifunctional organocatalysts readily available from naturally occurring molecules: saccharides and amino acids. The efficiency of the organocatalysts was demonstrated in the asymmetric Morita-
Enantioselective Morita-Baylis-Hillman reaction organocatalyzed by glucose-based phosphinothiourea
Yang, Weihong,Sha, Feng,Zhang, Xin,Yuan, Kui,Wu, Xinyan
, p. 2652 - 2656 (2013/01/15)
A class of bifunctional phosphinothioureas derived from saccharide was developed as new organocatalysts for the enantioselective Morita-Baylis-Hillman reaction between acrylates and aldehydes. With 10 mol% of glucose-based phosphinothiourea 1d, the allylic alcohols were obtained in up to 96% yield and 83% ee under mild reaction conditions.
Enantioselective Morita-Baylis-Hillman reaction promoted by l-threonine-derived phosphine-thiourea catalysts
Han, Xiaoyu,Wang, Youqing,Zhong, Fangrui,Lu, Yixin
experimental part, p. 6734 - 6740 (2011/11/05)
A series of bifunctional phosphine-thiourea organic catalysts based on natural amino acid scaffolds were designed and prepared. l-Threonine-derived bifunctional phosphine catalysts were found to be very efficient in promoting asymmetric Morita-Baylis-Hillman (MBH) reaction of acrylates with aromatic aldehydes, affording the desired MBH adducts with up to 90% ee. To gain mechanistic insights into the reaction, the effects of adding various additives on the MBH reaction were investigated. We propose that the hydrogen bonding interactions between the thiourea moiety of the catalyst and the enolate intermediate are crucial for the stereochemical outcome of the reaction. The method described in this report may provide a practical solution to the enantioselective MBH reaction of simple acrylates.
Chiral phosphinothiourea-catalyzed asymmetric Morita-Baylis-Hillman reactions of acrylates with aromatic aldehydes
Yuan, Kui,Song, Hong-Liang,Hu, Yinjun,Wu, Xin-Yan
experimental part, p. 8185 - 8190 (2010/01/06)
A series of chiral bifunctional phosphinothioureas were synthesized and applied to the enantioselective Morita-Baylis-Hillman reaction of aromatic aldehydes with acrylates. In the presence of 8 mol % of organocatalyst 2e, the Baylis-Hillman adducts were o
Valine-derived phosphinothiourea as organocatalyst in enantioselective Morita-Baylis-Hillman reactions of acrylates with aromatic aldehydes
Gong, Jing-Jing,Yuan, Kui,Wu, Xin-Yan
experimental part, p. 2117 - 2120 (2010/03/04)
A new type of chiral bifunctional phosphinothiourea derived from l-valine is synthesized and used as an organocatalyst in the enantioselective Morita-Baylis-Hillman reaction of aromatic aldehydes with acrylates. The desired products were obtained in good
ASYMMETRIC SYNTHESIS OF 2-SUBSTITUTED ACRYLATE ESTERS
Brand, Maja,Drewes, Siegfried E.,Loizou, Georgia,Roos, Gregory H. P.
, p. 795 - 802 (2007/10/02)
Chiral 2-substituted acrylate esters are obtained from the reaction between aldehydes and acrylate esters masked with an "internal" chiral auxiliary.Initial studies show that a similar result is achived if S-(-)-retronecine is used as "external" chiral auxiliary.
