4383-08-8Relevant academic research and scientific papers
Kinetic resolution of aryl alkenylcarbinols catalyzed by Fc-PIP
Hu, Bin,Meng, Meng,Jiang, Shanshan,Deng, Weiping
, p. 1289 - 1294 (2012/08/28)
An effective kinetic resolution of a variety of aryl alkenylcarbinols catalyzed by nonenzymatic acyl transfer catalyst Fc-PIP was developed, affording corresponding unreacted alcohols in good to excellent ee value up to 99% and with selectivity factors up to 24.
QUINAZOLINONE-TYPE COMPOUNDS AS CRTH2 ANTAGONISTS
-
Page/Page column 116, (2012/05/04)
This application provides for compounds of the formula Formula I or a pharmaceutically acceptable salt thereof, wherein the individual variables are defined herein, as well as processes to prepare these compounds, pharmaceutical compositions comprising the same and their use in treating disease state associated with the CRTH2 receptor.
Synthesis of the c1-c14 fragment of sarcoglaucol-16-one via z -selective ando-type horner-wadsworth-emmons olefination
Gastl, Christoph,Laschat, Sabine
supporting information; experimental part, p. 2643 - 2651 (2010/10/01)
A synthetic strategy involving a Z-selective Horner-Wadsworth-Emmons olefination was developed for the preparation of the sarcoglaucolone precursor methyl (2Z,6E)-8-(methoxymethoxy)-6-methyl-2-[(3E)-4-methyl-5-oxopent-3-enyl]-9- [(trimethylsilyl)methyl]deca-2,6,9-trienoate. The target compound was isolated in a E/Z ratio of 17:83 Georg Thieme Verlag Stuttgart New York.
Enantioselective synthesis of allylic alcohols via an oxazaborolidinium ion catalyzed diels-alder/retro-diels-alder sequence
Jones, Simon,Valette, Damien
supporting information; experimental part, p. 5358 - 5361 (2010/01/19)
A triflimide-activated oxazaborolidine catalyst successfully promoted the asymmetric Diels-Alder reaction of 9-methylanthracene with methacrolein in high regio- and enantioselectivity. The cycloadduct obtained was subsequently used as a chiral template to
A highly enantioselective synthesis of chiral allylic alcohols by asymmetric addition of novel mixed reagents of trialkenylbismuthines/dialkylzincs to aldehydes
Sato, Itaru,Asakura, Noriaki,Iwashita, Taizo
, p. 2638 - 2642 (2008/04/05)
A novel mixture of reagents of trialkenylbismuthines/dialkylzincs was developed and applied toward the synthesis of chiral allylic alcohols. The chiral β-amino alcohols catalyzed addition of the mixed reagents of trialkenylbismuthines/dialkylzincs to alde
A Tellurium Transposition Route to Allylic Alcohols: Overcoming Some Limitations of the Sharpless-Katsuki Asymmetric Epoxidation
Dittmer, Donald C.,Discordia, Robert P.,Zhang, Yanzhi,Murphy, Christopher K.,Kumar, Archana,et al.
, p. 718 - 731 (2007/10/02)
Good yields of enantiomeric allylic alcohols can be obtained in high enantiomeric excess (ee) by combining Sharpless-Katsuki asymmetric epoxidation process (SAE) with tellurium chemistry.The advantages of the tellurium process are as follows: (1) the 50percent yield limitation on the allylic alcohol in the Sharpless kinetic resolution (SKR) can be overcome; (2) allylic tertiary alcohols which are unsatisfactory substrates in the SKR can be obtained in high optical purity; (3) optically active secondary allylic alcohols with tertiary alkyl substituents (e.g. tert-butyl) at C-1 can be obtained in high ee; (4) optically active sterically congested cis secondary alcohols can be obtained in high ee; and (5) the nuisance of the slow SAE of some vinyl carbinols can be avoided.The key step in the reaction sequence is either a stereospecific 1,3-transposition of double bond and alcohol functionalities or an inversion of the alcohol configuration with concomitant deoxygenation of the epoxide function in epoxy alcohols.Trans secondary allylic alcohols can be converted to cis secondary allylic alcohols by way of erythro epoxy alcohols (glycidols); threo glycidyl derivatives are converted to trans secondary allylic alcohols.These transformations are accomplished by the action of telluride ion, generated in situ from the element, on a glycidyl sulfonate ester.Reduction of elemental Te is conveniently done with rongalite (HOCH2SO2Na) in an aqueous medium.This method is satisfactory when Te2- is required to attack at primary carbon site of a glycidyl sulfonate.In cases where Te2- is required to attack a secondary carbon site, reduction of the tellurium must be done with NaBH4 or LiEt3BH.Elemental tellurium is precipitated during the course of the reactions and can be recovered and reused.
NOVEL SYNTHESIS OF MONOFLUOROCYCLOBUTANES BY THE RING EXPANSION-FLUORINATION OF CYCLOPROPYLMETHANOLS WITH AN AMINE-METAL FLUORIDE-PYRIDINIUM POLY(HYDROGEN FLUORIDE)-COMPLEX
Kanemoto, Shigekazu,Shimuzu, Makoto,Yoshioka, Hirosuke
, p. 6313 - 6316 (2007/10/02)
Various new 1-fluoro-1-alkyl(or aryl)-2-substituted cyclobutanes were synthesized stereoselectively from 1-alkyl(or aryl)cyclopropyl carbinols by the ring expansion-fluorination using (iPr)2-KHF2-(HF)n.Py, and 2
