Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde.
نویسندگان
چکیده
[reaction: see text] Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with methoxy and dimethoxy acetaldehyde and furnishes (R)-2-hydroxy-3-methoxy-1-arylpropan-1-one and (R)-2-hydroxy-3,3-dimethoxy-1-arylpropan-1-one in high yields and enantiomeric excess via acyloin linkage. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to carboligation.
منابع مشابه
Benzaldehyde lyase catalyzed enantioselective self and cross condensation reactions of acetaldehyde derivatives.
Flexible protected 1,3,4-trihydroxy-2-butanone is synthesized in high enantiomeric excesses by using asymmetric homo- and cross- acyloin coupling of aliphatic aldehydes catalyzed by benzaldehyde lyase.
متن کاملKinetics and specificity of guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase towards substituted benzaldehydes.
Molybdenum-containing enzymes, aldehyde oxidase and xanthine oxidase, are important in the oxidation of N-heterocyclic xenobiotics. However, the role of these enzymes in the oxidation of drug-derived aldehydes has not been established. The present investigation describes the interaction of eleven structurally related benzaldehydes with guinea pig liver aldehyde oxidase and bovine milk xanthine ...
متن کاملEnantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me3SiCF2SO2Ph and PhSO2CF2H reagents catalyzed by chiral quaternary ammonium salts
BACKGROUND Although the nucleophilic difluoromethylation of aldehydes, ketones, and imines has been realized with PhSO(2)CF(2)H and related reagents, there are still no reports on the enantioselective nucleophilic reactions. RESULTS With a chiral quaternary ammonium salt as the catalyst and KOH as the base, we describe the first enantioselective difluoromethylation of aromatic aldehydes with ...
متن کاملApplication of a Polymer-Bound Thiazolium Salt to the Synthesis of Alpha-Hydroxy Ketones with an Aromatic and Aliphatic Substituent (Bencyloins) [1]
Alpha-Hydroxy ketones with an aromatic and aliphatic substituent were prepared with condensation of aromatic and aliphatic aldehydes in the presence of polymer-bound thiazolium salt.
متن کاملAromatic aldehydes as substrates for yeast and yeast alcohol dehydrogenase.
The conversion of benzaldehyde to optically active L-phenylacetyl carbinol by yeast fermentation is a key step in the manufacture of L-ephedrine. ’ Typical fermentation raw materials are molasses, which provides a source of hexoses for glycolysis, and benzaldehyde. L-phenylacetyl carbinol formation is catalyzed by the pyruvate decarboxylase complex.’ In the carboligase reaction, pyruvate is dec...
متن کاملذخیره 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 ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic letters
دوره 5 12 شماره
صفحات -
تاریخ انتشار 2003