Tertiary amide-based Knoevenagel-type reactions: a direct, general, and chemoselective approach to enaminones.
نویسندگان
چکیده
We report one-pot and chemoselective Knoevenagel-type reactions using highly stable amides and lactams as the electrophilic substrates. The method is based on the in situ activation of amide carbonyl with triflic anhydride and a subsequent reaction with carbanions generated in situ from carbonyl compounds. The amide-based method is an alternative to the versatile thioamide-based Eschenmoser sulfide contraction.
منابع مشابه
Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(i) bis-metal sequential catalysis.
We report herein a convenient and versatile method for the direct reductive alkynylation of tertiary amides to give propargylic amines through sequential Ir-catalysed hydrosilylation-Cu(i)-catalysed alkynylation. The reactions proceed chemoselectively at the amide group in the presence of several sensitive functional groups including the very reactive aldehyde group on either the amide or the a...
متن کاملCatalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide.
Organofluorine compounds are found in several important classes of chemicals, such as pharmaceuticals, agrochemicals, and functional materials. Chemists have been immensely interested in the development of methodologies for expeditious access to fluorine containing building blocks. In this study, we report a new method for the catalytic asymmetric synthesis of CF3-substituted tertiary propargyl...
متن کاملZnCl2-catalyzed chemoselective cascade reactions of enaminones with 2-furylcarbinols: a versatile process for the synthesis of cyclopenta[b]pyrrole derivatives.
A highly efficient ZnCl2-catalyzed cascade reaction of enaminones with 2-furylcarbinols under mild reaction conditions has been developed. This methodology offers a chemo- and diastereo-selective access to functionalized cyclopenta[b]pyrrole derivatives in good to excellent yields.
متن کاملPreparation of functional benzofurans and indoles via chemoselective intramolecular Wittig reactions.
A general preparation of new types of benzofurans, benzothiophenes and indoles is realized via chemoselective intramolecular Wittig reactions with the corresponding ester, thioester and amide functionalities using in situ formed phosphorus ylides as key intermediates. The reaction conditions are very mild, and numerous Michael acceptors and commercially available acid chlorides can be applied v...
متن کاملCatalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide† †Electronic supplementary information (ESI) available. CCDC 1498994–1498996. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc00330g Click here for additional data file.Click here for additional data file.
Organofluorine compounds are found in several important classes of chemicals, such as pharmaceuticals, agrochemicals, and functional materials. Chemists have been immensely interested in the development of methodologies for expeditious access to fluorine containing building blocks. In this study, we report a new method for the catalytic asymmetric synthesis of CF3-substituted tertiary propargyl...
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 communications
دوره 50 63 شماره
صفحات -
تاریخ انتشار 2014