Diastereoselective oxidative α-amination of aliphatic aldehydes catalyzed by iodine: synthesis of syn-γ-hydroxy-α-amino acetals.
نویسندگان
چکیده
Aldehydes can react with secondary amines to give α-amino acetals via the α-amination of aliphatic aldehydes catalyzed by iodine. The presence of an asymmetric hydroxylated center at the γ-position of the aldehyde was found to induce the stereoselective amino group. This method represents a stereoselective α-amination of γ-hydroxyaldehydes for the synthesis of syn-γ-hydroxy-α-amino acetals in good yields and reasonable diastereoselectivities under very mild conditions.
منابع مشابه
Catalytic Asymmetric Direct Aldol Reaction of α-Alkyl Azlactones and Aliphatic Aldehydes.
An unprecedented highly diastereoselective and enantioselective aldol reaction of α-alkyl azlactones and aliphatic aldehydes was achieved with cinchona alkaloid catalysts. To our knowledge, this reaction provides the first useful catalytic asymmetric access toward β-hydroxy-α-amino acids bearing alkyl substituents, which are structural motifs embedded in many natural products.
متن کاملRegio- and diastereoselective nickel-catalyzed allylation of aromatic aldehydes with α-halo-β,β-difluoropropene derivatives.
A one-pot nickel-catalyzed allylation of aromatic aldehydes with α-halo-β,β-difluoropropene-containing compounds promoted by ZnEt(2) under mild conditions was described. The reaction displays moderate to good regio- and diastereoselectivity, tolerates a wide range of functional groups, and provides an efficient method for the synthesis of γ-fluorinated homoallylic alcohols.
متن کاملDevelopment of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters
A zinc-ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation operates at room temperature and affords syn β-hydroxy-α-amino esters in high yields with good to excellent levels of di...
متن کاملChromium(II)-Catalyzed Diastereoselective Pinacol Type Cross Coupling between α,β-Unsaturated Carbonyl Compounds and Aliphatic Aldehydes
Synlett 2002, No. 12, Print: 02 12 2002. Art Id.1437-2096,E;2002,0,12,2015,2018,ftx,en;G26802ST.pdf. © Georg Thieme Verlag Stuttgart · New York ISSN 0936-5214 Abstract: Using only 10 mol% of CrCl2 as catalyst, acroleins and , -unsaturated ketones were coupled with aliphatic aldehydes to obtain substituted 1,2-diols using manganese powder as reducing agent and TMS-Cl as scavenger. Diastereoselec...
متن کاملRu/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to aliphatic aldehydes and α-ketoesters.
A ruthenium-catalyzed asymmetric arylation of aliphatic aldehydes and α-ketoesters with arylboronic acids has been developed, giving chiral alkyl(aryl)methanols and α-hydroxy esters in good yields. The use of a chiral bidentate phosphoramidite ligand (Me-BIPAM) achieved excellent enantioselectivities.
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 & biomolecular chemistry
دوره 11 48 شماره
صفحات -
تاریخ انتشار 2013