Chiral Phosphoric Acid-Catalyzed Desymmetrization of meso-Aziridines with Functionalized Mercaptans
نویسندگان
چکیده
منابع مشابه
Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines.
An amino-indanol derived chiral guanidine was developed as an efficient Brønsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities.
متن کاملChiral magnesium(II)-catalyzed asymmetric ring-opening of meso-aziridines with primary alcohols.
The asymmetric ring-opening of meso-aziridines with primary alcohols is realized using an N,N'-dioxide-Mg(OTf)2 complex as the catalyst. The desired vicinal trans-β-amino ethers are afforded in good yields and enantioselectivities. Aniline and water could also be used as the nucleophiles for the ring-opening in an identical catalyst system.
متن کاملDirect amino acid-catalyzed asymmetric desymmetrization of meso-compounds: tandem aminoxylation/O-N bond heterolysis reactions.
[reaction: see text] A practical organocatalytic process for the synthesis of optically active, highly substituted alpha-hydroxy-ketones was achieved through asymmetric desymmetrization (ADS) of prochiral ketones. The ADS and O-N bond reduction reaction of prochiral ketone with nitrosobenzene in the presence of a catalytic amount of chiral amine or amino acid produced the tandem ADS/O-N bond re...
متن کاملPhosphoric acid functionalized pre-sintered meso-silica for high temperature proton exchange membrane fuel cells.
An inorganic proton exchange membrane based on sintered mesoporous silica and phosphoric acid was developed with a high proton conductivity of 0.06 S cm(-1) at 200 °C, achieving an excellent power output of 689 mW cm(-2) in H2 at 190 °C and 200 mW cm(-2) in methanol at 200 °C with no external humidification.
متن کاملEnantioselective synthesis of fused heterocycles with contiguous stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking.
Described herein is a highly enantioselective synthesis of fused piperidine and pyrrolidine derivatives with all-carbon stereogenic centers. The enantioselective reductive amination from C(s)-symmetric 1,3-dione derivatives proceeded in a highly stereoselective manner by taking advantage of the desymmetrization approach to afford fused heterocycles with contiguous stereogenic centers in good to...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2009
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol902123h