Catalytic Asymmetric Direct Aldol Reaction of α-Alkyl Azlactones and Aliphatic Aldehydes.
نویسندگان
چکیده
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.
منابع مشابه
ProPhenol-Catalyzed Asymmetric Additions by Spontaneously Assembled Dinuclear Main Group Metal Complexes
The development of catalytic enantioselective transformations has been the focus of many research groups over the past half century and is of paramount importance to the pharmaceutical and agrochemical industries. Since the award of the Nobel Prize in 2001, the field of enantioselective transition metal catalysis has soared to new heights, with the development of more efficient catalysts and ne...
متن کاملThe direct catalytic asymmetric aldol reaction of α-substituted nitroacetates with aqueous formaldehyde under base-free neutral phase-transfer conditions.
Enantioselective direct aldol reaction of α-substituted nitroacetates with aqueous formaldehyde for the synthesis of α-alkyl serines has been achieved under base-free neutral phase-transfer conditions with a bifunctional chiral phase-transfer catalyst.
متن کاملCatalytic application of 3-methyl-1-sulfonic acid imidazolium tetrachloroferrate as nanostructured catalyst on the cross-aldol condensation reaction of cycloalkanones with aldehydes
3-methyl-1-sulfonic acid imidazolium tetrachloroferrate {[Msim]FeCl4} as an efficient sulfur catalyst was prepared and applied, as an efficient catalyst, for the cross-aldol condensation reaction between cycloalkanones and arylaldehydes to give α,αʹ- bis(arylidene)cycloalkanones in high yields and short reaction times at 75 °C under solvent-free conditions. 3-methyl-1-sulfonic acid imidazolium...
متن کاملDirect asymmetric aldol-Tishchenko reaction of aliphatic ketones catalyzed by syn-aminoalcohol-Yb(III) complexes.
The asymmetric direct aldol condensation of aldehydes with ethyl- and propylketones is catalyzed by syn-alpha-aminoalcohol-Yb(OTf)3 complexes, yielding the anti-1,3-diol monoesters with high diastereocontrol and good enantioselectivity. Three adjacent stereogenic centers are created in a simultaneous aldol condensation and Evans-Tishchenko reduction in an acyclic system.
متن کاملAmino acid catalyzed direct asymmetric aldol reactions: a bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions.
Direct asymmetric catalytic aldol reactions have been successfully performed using aldehydes and unmodified ketones together with commercially available chiral cyclic secondary amines as catalysts. Structure-based catalyst screening identified L-proline and 5,5-dimethyl thiazolidinium-4-carboxylate (DMTC) as the most powerful amino acid catalysts for the reaction of both acyclic and cyclic keto...
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:
- Chemical science
دوره 6 11 شماره
صفحات -
تاریخ انتشار 2015