85157-57-9Relevant academic research and scientific papers
Optical resolution of C2-symmetric racemic 1,4-diols with o-xylylene structure by chiral resolving agent (S)-ALBO-V
Asami, Masatoshi,Zhong, Lvling,Sekiguchi, Naoki,Yamada, Kumiko,Hiwatashi, Yuya,Taniguchi, Toshiro,Hosoda, Naoya,Ito, Suguru
supporting information, p. 966 - 968 (2015/09/01)
Optical resolution of C2-symmetric racemic 1,4-diols, 1,2-bis(1-hydroxyalkyl)benzene, was examined using (S)-5-allyl-2-oxabicyclo[3.3.0]octene ((S)-ALBO-V) as chiral resolving agent. Diastereomeric acetals obtained from the 1,4-diols with (S)-A
NEW CHIRAL DIOLS, THEIR MANUFACTURE AND LIGANDS AND CATALYSTS DERIVED THEREFROM
-
Page 26-27, (2008/06/13)
The present invention relates to a method for the preparation of C2-symmetric 1,4-diols of the formula IVA or IVB, wherein ring A, R1 and R2 have the meanings given in the specification, that makes use of the metallation of pure enantiomers of α-(aryl or heteroaryl)-α-substituted alkanol compounds or the use of said alkanol compounds in the preparation of said mmetric 1,4-diols; novel C2--symmetric 1,4-diols in enantiomerically pure form; and methods of use or their use in the synthesis of chiral ligands which find use to produce catalysts for a variety of asymmetric transformations such as hydrogenations.
Synthesis of α,β-unsaturated dioxanes, dioxolanes and dioxepanes by trans-acetalisation of dimethylacetals with meso or C 2-symmetrical 1,2-, 1,3- and 1,4-diols
Lemiègre, Lo?c,Lesetre, Fleur,Combret, Jean-Claude,Maddaluno, Jacques
, p. 415 - 427 (2007/10/03)
Several o-dibenzylic diols were prepared reacting organometallics with o-phthalaldehyde at room temperature in ether. The identity of the meso and C2-symmetrical (D,L) isomers as well as their ratio were determined by chiral gas chromatography. The meso and C2 (racemic) stereoisomeric diols were easily separated by flash chromatography on silica gel. A set of 18 α,β-unsaturated acetals were then prepared reacting those, as well as commercially available 1,2, 1,3 and 1,4 diols, with the corresponding methylacetals in acidic medium. A trans-acetalisation procedure adapted to the cases of fragile allylic alcohols or unfavorable 1,6 diols-derived dioxonanes based on a Dean-Stark trapping of methanol was also employed.
An efficient enantioselective preparation of (S,S)-1,2-bis(1-hydroxyalkyl)benzene
Asami, Masatoshi,Wada, Masaaki,Furuya, Sanae
, p. 1110 - 1111 (2007/10/03)
(S,S)-1,2-Bis(1-hydroxyalkyl)benzenes were obtained in >99% ee's with high diastereoselectivity by the enantioselective addition of dialkylzinc to (S)-2-[1-(4-methoxybenzyloxy)alkyl]-benzaldehyde (86% ee) in the presence of a catalytic amount of (S)-2-(4-
Enantioselective dialkylation of 1,2-phthalicdicarboxaldehyde
Kleijn, Henk,Jastrzebski, Johann T.B.H.,Boersma, Jaap,Van Koten, Gerard
, p. 3933 - 3937 (2007/10/03)
A new two-step, one-pot procedure is reported for the enantioselective synthesis of C2-symmetric diols derived from 1,2-phthalicdicarboxaldehyde. The first step involves the enantioselective addition of a dialkylzinc compound to one of the aldehyde groups, affording a lactol organozinc derivative. In the second step this lactol derivative is converted to the appropriate diol with the aid of a Grignard reagent and subsequent hydrolysis. This methodology also allows the synthesis of unsymmetric diols.
Asymmetric synthesis of chiral diols by the catalytic enantioselective dialkylation of tere-, iso-, and phthalaldehydes and by a catalytic enantioselective autoinductive reaction
Soai, Kenso,Inoue, Yukikazu,Takahashi, Tomohide,Shibata, Takanori
, p. 13355 - 13362 (2007/10/03)
Optically pure aromatic diols were synthesized by the highly enantioselective dialkylation of aromatic dialdehydes with dialkylzincs in the presence of a catalytic amount of chiral aminoalcohol 1 or chiral thiophosphoramide alcohol 2 with Ti(0-i-Pr)4. The chiral titanium(IV) alkoxide of 4b, a diisopropylated product of isophthalaldehyde, catalyzed the addition of diisopropylzinc to isophthalaldehyde to gave a chiral zinc alkoxide of 4b with the same configuration by an enantioselective autoinductive reaction (up to 44% e.e.).
