A stereodivergent asymmetric approach to difluorinated aldonic acids.

نویسندگان

  • Christophe Audouard
  • Igor Barsukov
  • John Fawcett
  • Gerry A Griffith
  • Jonathan M Percy
  • Stéphane Pintat
  • Clive A Smith
چکیده

A (bromodifluoromethyl)alkyne has been deployed in a stereoselective route to difluorinated aldonic acid analogues, in which a Sharpless asymmetric dihydroxylation reaction and diastereoisomer separation set the stage for phenyl group oxidation.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters

The catalytic asymmetric allylboration of cyclic imines with γ,γ-disubstituted allylboronic acids provides products with adjacent stereocenters in high yield and stereoselectivity. Various electrophiles, including 3,4-dihydroisoquinolines and indoles, were prenylated in a fully stereodivergent fashion by switching the E/Z geometry of the allylboronate and/or the enantiomer of the BINOL catalyst...

متن کامل

Stereodivergent Organocatalytic Intramolecular Michael Addition/Lactonization for the Asymmetric Synthesis of Substituted Dihydrobenzofurans and Tetrahydrofurans

A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)-(-)-tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r.syn/anti , 99 % eesyn ), whereas using a cinchona alkaloid derived...

متن کامل

High-speed Liquid Chromatography of Sugar Acids on An- Ion-exchange Resins

Mixtures of aldonic and aldaric acids are difficult to analyse. Aldonic acids can be separated in a satisfactory way on anion-exchange resins with a solution of sodium chloride as eluent. Under these circumstances, however, aldaric acids show unacceptably long elution times and peak broadening. The ability of aldaric acids to form non-adsorbable complexes with magnesium ions lowers their elutio...

متن کامل

Simultaneous Separation and Quantitative Determination of Monosaccharides, Uronic Acids, and Aldonic Acids by High Performance Anion- Exchange Chromatography Coupled with Pulsed Amperometric Detection in Corn Stover Prehydrolysates

A method for simultaneous separation and quantitative determination of arabinose, galactose, glucose, xylose, xylonic acid, gluconic acid, galacturonic acid, and glucuronic acid was developed by using high performance anion-exchange chromatography coupled with pulsed amperometric detection (HPAEC-PAD). The separation was performed on a CarboPac TM PA-10 column (250 mm × 2 mm) with a various gra...

متن کامل

Characteristics and Kinetics of the Aldonic Acids Production using Whole-cell catalysis of Gluconobacter oxydans

The characteristics and kinetics of whole-cell catalysis were investigated individually or simultaneously relative to the bio-oxidation of five monosaccharides to corresponding aldonic acids using Gluconobacter oxydans. For individual catalysis, 30 g/L glucose could be consumed completely at 3.21 g/L/h in 8 h, and arabinose was the slowestconsumed at 1.18 g/L/h in 8 h. Among five monosaccharide...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Chemical communications

دوره 13  شماره 

صفحات  -

تاریخ انتشار 2004