Asymmetric Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes.
نویسندگان
چکیده
An efficient diastereo- and enantioselective Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes has been developed. This asymmetric Friedel-Crafts alkylation led to medicinally privileged indolyl(nitro)chromans in good yields with high enantioselectivities (up to 95% ee) and diastereoselectivities under mild reaction conditions.
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 کاملHighly enantioselective Friedel-Crafts alkylations of pyrroles and indoles with alpha'-hydroxy enones under Cu(II)-simple bis(oxazoline) catalysis.
Remarkably high and regular enantioselectivities are obtained in Friedel-Crafts alkylation reactions involving alpha'-hydroxy enone templates and Cu(II)-bis(oxazoline) complexes as catalysts. The simple elaboration of adducts provides a route to enantioenriched aldehydes, carboxylic acids, and ketones containing the pyrrole and indole frameworks.
متن کاملEnantioselective indole Friedel--Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.
A highly enantioselective Friedel-Crafts alkylation of electron-rich aromatic nucleophiles catalyzed by scandium(III) triflate-pyridyl(bis)oxazoline complexes has been accomplished. The reaction involves alpha,beta-unsaturated acyl phosphonates as electrophiles and primarily substituted indoles as nucleophiles. The reactive acyl phosphonate product is converted to the corresponding ester or ami...
متن کاملAmmonium monovanadate: a versatile and reusable catalyst for Friedel-Crafts alkylation and Michael addition of indoles
Ammonium monovanadate (NH4VO3) has been devoted as an efficient, commercially available, eco-friendly and reusable catalyst for the synthesis of bis(indolyl)methanes (BIMs), oxindole derivatives and also Michael adducts of indoles at 50 °C under solvent-free conditions. The reusability of this solid acid catalyst in addition with its selectivity has also been examined.
متن کاملAmmonium monovanadate: a versatile and reusable catalyst for Friedel-Crafts alkylation and Michael addition of indoles
Ammonium monovanadate (NH4VO3) has been devoted as an efficient, commercially available, eco-friendly and reusable catalyst for the synthesis of bis(indolyl)methanes (BIMs), oxindole derivatives and also Michael adducts of indoles at 50 °C under solvent-free conditions. The reusability of this solid acid catalyst in addition with its selectivity has also been examined.
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 10 24 شماره
صفحات -
تاریخ انتشار 2012