77118-87-7Relevant articles and documents
Enantioselective Synthesis of Homo-allylic Alcohols from Chiral Allylic Tin(IV) (+)-Diethyl Tartrate Complexes and Aldehydes
Boldrini, Gian Paolo,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 685 - 686 (1986)
A quite simple procedure to synthesize optically active secondary homoallylic alcohols from the reaction between aldehydes and allylic tin(IV) complexes containing (+)-diethyl tartrate as chiral auxiliary ligand is reported.
An enantioselective allylation reaction of aldehydes in an aqueous medium
Loh, Teck-Peng,Zhou, Jian-Rong
, p. 9115 - 9118 (1999)
An enantioselective allylation reaction of aldehydes with enantioselectivities up to 92% has been achieved in an aqueous medium, by using (S,S)-2,6-bis(4-isopropyl-2-oxazolin-2-yl)pyridine as the chiral source.
Synthesis of polysaccharide derivatives bearing pyridine N-oxide groups and their use as asymmetric organocatalysts
Ikai, Tomoyuki,Moro, Munetsugu,Maeda, Katsuhiro,Kanoh, Shigeyoshi
, p. 1055 - 1058 (2011)
Novel amylose and cellulose derivatives bearing pyridine N-oxide groups were synthesized, and their performance as asymmetric organocatalysts was investigated. The amylose derivatives bearing 3-pyridyl N-oxide groups enantioselectively catalyzed the allyl
Chiral sulfoxides in the enantioselective allylation of aldehydes with allyltrichlorosilane: A kinetic study
Monaco, Guglielmo,Vignes, Chiara,De Piano, Francesco,Bosco, Assunta,Massa, Antonio
, p. 9650 - 9659 (2012)
The mechanism of the allylation of aldehydes in the presence of allyltrichlorosilane employing the commercially available (R)-methyl p-tolyl sulfoxide as a Lewis base has been investigated. The combination of kinetic measurements, conductivity analysis an
Pd(II)-catalyzed intermolecular direct C-H bond iodination: An efficient approach toward the synthesis of axially chiral compounds via kinetic resolution
Gao, De-Wei,Gu, Qing,You, Shu-Li
, p. 2741 - 2745 (2014)
An efficient protocol to synthesize axially chiral compounds via kinetic resolution by Pd(II)-catalyzed direct C-H iodination was realized (up to s = 27). The iodide product could be easily transformed to aryl-substituted pyridine N-oxides via the Suzuki-
Enantioselective Allylation of Oxocarbenium Ions Catalyzed by Bi(OAc)3/Chiral Phosphoric Acid
Cheng, Jin-Pei,Li, Xin,Pan, Yu-Liang,Wang, Jie,Yang, Chen,Zheng, Han-Liang
, p. 8069 - 8076 (2020)
Phthalides as the crucial core skeletons are found extensively in natural products and biological active molecules. Herein we disclose an asymmetric allylation of 3-hydroxyisobenzofuran-1(3H)-ones with boron allylation reagents to construct chiral phthali
Emergence of Highly Enantioselective Catalytic Activity in a Helical Polymer Mediated by Deracemization of Racemic Pendants
Ikai, Tomoyuki,Ando, Mitsuka,Ito, Masaki,Ishidate, Ryoma,Suzuki, Nozomu,Maeda, Katsuhiro,Yashima, Eiji
supporting information, p. 12725 - 12735 (2021/08/24)
Any polymers composed of racemic repeating units are obviously optically inactive and hence chiral functions, such as asymmetric catalysis, will not be expected at all. Contrary to such a preconceived notion, we report an unprecedented helical polymer-based highly enantioselective organocatalyst prepared by polymerization of a racemic monomer with no catalytic activity. Both the right- and left-handed helical poly(biarylylacetylene)s (PBAs) composed of dynamically racemic 2-arylpyridyl-N-oxide monomer units with N-oxide moieties located in the vicinity of the helical polymer backbone can be produced by noncovalent interaction with a chiral alcohol through deracemization of the biaryl pendants. The macromolecular helicity and the axial chirality induced in the PBAs are retained ("memorized") after complete removal of the chiral alcohol. Accordingly, the helical PBAs with dual static memory of the helicity and axial chirality show remarkable enantioselectivity (86% ee) for the asymmetric allylation of benzaldehyde. The enantioselectivity is slightly lower than that (96% ee) of the homochiral PBAs prepared from the corresponding enantiopure (R)- and (S)-monomers, but is comparable to that (88% ee) of the helical PBA composed of nonracemic monomers of ca. 60% ee.
Highly Enantioselective Allylation Reactions of Aldehydes with Allyltrimethylsilane Catalyzed by a Chiral Oxazaborolidinium Ion
Kim, Taehyeong,Jeong, Hye-Min,Venkateswarlu, Anipireddy,Ryu, Do Hyun
supporting information, p. 5198 - 5201 (2020/07/15)
A highly enantioselective allylation reaction of aldehydes with silyl reagents was developed for the synthesis of a variety of chiral homoallylic alcohols. In the presence of a chiral oxazaborolidinium ion (COBI) catalyst, the reaction proceeded in high yield (up to 99percent) with excellent asymmetric induction (up to 99percent ee).