78038-79-6Relevant academic research and scientific papers
Solution-phase synthesis and evaluation of tetraproline chiral stationary phases
Dai, Zhi,Ye, Guozhong,Pittman Jr., Charles U.,Li, Tingyu
experimental part, p. 329 - 338 (2012/05/20)
A protocol was developed for the solution-phase synthesis of multigram amounts of two 9-fluorenylmethoxycarbonyl (Fmoc)-protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution-phase-synthesized tetraproline CSPs with that prepared by stepwise solid-phase synthesis revealed that all three had similar chromatographic performance for resolving 53 model analytes. This suggests that the solution-phase synthesis of oligoprolines, which allows for the specific benefits of good batch reproducibility, selector homogeneity, and possibly low cost, is a feasible alternative to the solid-phase synthesis of oligoproline CSPs. Copyright
Combinatorial approach for the design of new, simplified chiral phase-transfer catalysts with high catalytic performance for practical asymmetric synthesis of α-alkyl-α-amino acids
Kitamura, Masanori,Arimura, Yuichiro,Shirakawa, Seiji,Maruoka, Keiji
, p. 2026 - 2030 (2008/09/19)
A very efficient, chiral phase-transfer catalyst (S)-2Db was prepared by taking advantage of the combinatorial approach from the known, easily available (S)-1,1′-binaphthyl-2,2′-dicarboxylic acid. This catalyst exhibited the high catalytic performance (0.
Reductive ring opening of dihydrodibenzothiepine and dihydrodinaphtho- oxepine and -thiepine
Foubelo, Francisco,Moreno, Benjamín,Soler, Tatiana,Yus, Miguel
, p. 9082 - 9096 (2007/10/03)
The 4,4′di-tert-butylbiphenyl (DTBB)-catalysed lithiation of dihydrodibenzothiepine (1) at -78°C for 30 min followed by reaction with a carbonyl compound [tBuCHO, Ph(CH2)2CHO, PhCHO, (n-C5H11)2/
Facile synthesis of enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acid via lipase-catalyzed kinetic resolution
Furutani, Toshiyuki,Hatsuda, Masanori,Imashiro, Ritsuo,Seki, Masahiko
, p. 4763 - 4768 (2007/10/03)
Enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acids (R)-1 and (S)-1 have been synthesized through the lipase-catalyzed kinetic resolution of the racemic 2,2-bis(hydroxymethyl)-1,1'-binaphthyl (±)-2 and subsequent oxidation of the hydroxymethyl groups. (C) 2000 Elsevier Science Ltd.
C2 Symmetric Amines. II. Asymmetric Synthesis of C2 (3S,3'S)-and (3R,3'R)Dimethyl 4H-DinaphthAzepines
Meyers, A. I.,Nguyen, Thanh H.
, p. 5873 - 5876 (2007/10/02)
The C2-symmetric dimethyl amines (1a, 1b) were prepared in high stereoselectivity by carbanion alkylation of their respective formamidines.
Absolute configuration of 3,3'-Dihydroxy-4,4' -biphenanthryl as determined by the stereochemistry of cyclic diester formation with 1,1'-Binaphthyl-2,2'-dicarboxylic acid
Koike,Hattori,Miyano
, p. 1899 - 1900 (2007/10/02)
Condensation of racemic 3,3'-dihydroxy-4,4'-biphenanthryl [(±)-2] with (R)-1,1'binaphthyl-2,2'-dicarboxylic acid dichloride (5) allows cyclization of only (-)-2 to give the 12-membered cyclic diester (7), the absolute configuration of which can be assigned (R,R) from steric reasons. Thus, absolute stereochemistry of (-)-2 is determined to be (R).
The Asymmetric Ullmann Coupling Reaction of (S)-2,2'-Bis(1-bromo-2-naphthoyloxy)-1,1'-binaphtyl Revisited. Formation of 24-Membered Optically Pure Cyclic Dimer as Well as 12-Membered Cyclic Monomer
Miyano, Sotaro,Handa, Shigeru,Tobita, Masayuki,Hashimoto, Harukichi
, p. 235 - 238 (2007/10/02)
The copper-promoted Ullmann reaction of the title diester proceeded with high stereoselectivity to give 24-membered optically pure cyclic dimer of (S,S,S,S)-configuration as well as 12-membered monomeric cycle of (S,S)-configuration.The reaction also gave reduced, open-chain dimer enriched in (S,R,S)-diastereomer(S,S,S)-counterpart (17percent d.e.).Stereochemical course to the cyclic dimer was discussed considering the result that the intermolecular Ullmann coupling of chiral alcohol esters of 1-bromo-2-naphthoic acid poorly induced axial chirality in the joining of the two naphthyl units.
The Ullmann Coupling Reaction of Axially Chiral (S)-2,2'-Bis(1-iodo-2-naphtyloxycarbonyl)-1.1'-binaphthyl
Miyano, Sotaro,Shimizu, Kunitoshi,Sato, Shinya,Hashimoto, Harukichi
, p. 1345 - 1346 (2007/10/02)
The intramolecular Ullmann coupling of the title diester proceeded in low yield but with virtually complete asymmetric induction in joining the two naphthyl units leading to the 12-membered cyclic diester of (S,S)-configuration, which is the same diastereoisomer obtained from the reaction of (S)-2,2'-bis(1-bromo-2-naphthoyloxy)-1,1'-binaphthyl.
The Asymmetric Ullmann Coupling Reaction of Chiral Diol Diesters of 1-Bromo-2-naphthoic Acid and 2-Halo-3-nitrobenzoic Acids: Highly Diastereoselective Synthesis of Atropisomeric 6,6'-Dinitrodiphenic Acids
Miyano, Sotaro,Handa, Shigeru,Shimizu, Kunitoshi,Tagami, Katsuya,Hashimoto, Harukichi
, p. 1943 - 1947 (2007/10/02)
The copper-promoted Ullmann reaction of chiral diol diesters of 1-bromo-2-naphthoic acid induced axial dissymmetry into the newly formed 1,1'-binaphthyl bond: chiral diol, apparent net optical yield for the joining of two napphthyl units, and axial chirality induced are as follows: (S)-1,1'-binaphthyl-2,2'-diol, 71percent, S; (1S,2S)-1,2-diphenyl-1,2-ethanediol. 32percent, S; (1R,2R)-1,2-bis(ethoxycarbonyl)-1,2-ethanediol. 33percent.S; (4S,5S)-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane, 3.7percent, R.The reaction of (R)-1,1'-binaphthyl-2,2'-diol esters of 2-halo-3-nitrobenzoic acid gave up to 85percent net optical yield for the c oupling; the intramolecular cyclization proceeded with virtually complete diastereoselectivity to give cyclic diester of R,R-configuration in a 42percent isolated yield.This remarkable stereocontrol is ascribed to the steric requirement of the 12-membered cyclic diester structure containing rigid 1,1'-binaphthyl and 1,1'-biphenyl moiety.
