Sequential combination of Michael and acetalization reactions: direct catalytic asymmetric synthesis of functionalized 4-nitromethyl-chromans as drug intermediates.
نویسندگان
چکیده
Functionalized chiral 4-nitromethyl-chromans as drug intermediates were achieved for the first time through sequential combination of Michael and acetalization reactions on 2-(2-nitro-vinyl)-phenols with acetone and alcohols in the presence of a catalytic amount of 9-amino-9-deoxyepiquinine and Ph(2)CHCO(2)H followed by p-TSA.
منابع مشابه
Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
The enantioselective tandem Friedel-Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)2 complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99% ee).
متن کاملAlkanedisulfamic acid functionalized silica-coated magnetic nanoparticles as a reusable efficient nanocatalyst for synthesis of gem-dihydroperoxides and 1,2,4,5-tetraoxanes
Alkanedisulfamic acid functionalized silica-coated magnetic nanoparticles (ADSA-MNPs) were used as effective, low-cost and reusable solid heterogeneous nanomagnetic catalysts for conversion of aldehydes and ketones to corresponding gem-dihydroperoxides and 1,2,4,5-tetraoxanes using aqueous hydrogen peroxide (30% w/w in H2O) at room temperature. These compounds are important ...
متن کاملAlkanedisulfamic acid functionalized silica-coated magnetic nanoparticles as a reusable efficient nanocatalyst for synthesis of gem-dihydroperoxides and 1,2,4,5-tetraoxanes
Alkanedisulfamic acid functionalized silica-coated magnetic nanoparticles (ADSA-MNPs) were used as effective, low-cost and reusable solid heterogeneous nanomagnetic catalysts for conversion of aldehydes and ketones to corresponding gem-dihydroperoxides and 1,2,4,5-tetraoxanes using aqueous hydrogen peroxide (30% w/w in H2O) at room temperature. These compounds are important ...
متن کاملDeep Eutectic Solvent Based on Choline Chloride/Urea as an Efficient Catalytic System for the One-Pot Synthesis of Highly Functionalized 1,4-Dihydropyridines and Polysubstituted 4H-Chromenes
One-pot four-component synthesis of polyfunctionalized 1,4-dihydropyridine derivatives was developed by a condensation of aldehydes, malononitrile, diethylacetylenedicarboxylate and aniline in the presence of choline chloride/urea as a deep eutectic solvent (DES)at room temperature.Moreover, an efficient method was reported for the synthesis of highly substituted 4H-chromenes through one-...
متن کاملCatalytic Direct Asymmetric Michael Reactions: Addition of Unmodified Ketone and Aldehyde Donors to Alkylidene Malonates and Nitro Olefins Catalytic Direct Asymmetric Michael Reactions
SYNTHESIS 2004, No. 9, pp 1509–1521xx.xx.2004 Advanced online publication: 26.05.2004 DOI: 10.1055/s-2004-822392; Art ID: C0404SS © Georg Thieme Verlag Stuttgart · New York Abstract: The Michael additions of a number of ketones and aldehydes to alkylidene malonates and nitro olefins were studied. The reactions employ small organic molecules as catalyst under mild reaction conditions and do not ...
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 8 19 شماره
صفحات -
تاریخ انتشار 2010