Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters.
نویسندگان
چکیده
An unprecedented stereoselective organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence between β-dicarbonyl compounds, β-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has been developed. The protocol opens an efficient entry to isoxazole bearing cyclohexanes with six consecutive stereogenic centers including one tetrasubstituted carbon in good yields and excellent diastereo- and enantioselectivities.
منابع مشابه
Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters† †Electronic supplementary information (ESI) available. CCDC 1037530. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4cc09730k
متن کامل
Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence† †Electronic supplementary information (ESI) available. CCDC 990847. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4cc01885k Click here for additional data file. Click here for additional data file.
A highly stereoselective one-pot procedure involving an enantioselective Michael addition promoted by low loading of an amino-squaramide catalyst followed by an achiral base catalyzed domino Michael-Knoevenagel-type 1,2-addition sequence provides efficient access to fully substituted cyclohexanes bearing five contiguous stereogenic centers in good yields (68-86%) and excellent stereoselectiviti...
متن کاملEnantioselective organocatalytic domino synthesis of tetrahydropyridin-2-ols.
The asymmetric synthesis of tetrahydropyridin-2-ols from enals and enaminones is described. The organocatalytic domino reaction involves a Michael addition-hemiaminalization sequence using the Jørgensen-Hayashi catalyst. Dehydration or oxidation leads to the corresponding 1,4-dihydro-pyridines or 3,4-dihydropyridin-2-ones in a one-pot fashion.
متن کاملOne-pot enantioselective construction of indoloquinolizidine derivatives bearing five contiguous stereocenters using aliphatic aldehydes, nitroethylenes, and tryptamine.
An organocatalytic cascade reaction was established for the construction of indoloquinolizidine derivatives bearing five contiguous stereocenters from readily available aliphatic aldehydes, nitroethylenes, and tryptamine. This one-pot process gave 30-55% overall yields with excellent d.r. (>20 : 1 in all cases) and ee (91-98%). Additionally, quaternary stereogenic carbon center-containing indol...
متن کاملZrP2O7 NPs: A recyclable, efficient heterogeneous catalyst for the synthesis of 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives via a multi-component reaction
ZrP2O7 nanoparticles (NPs) as an efficient catalyst have been used for the preparation of 1,6-diamino-2- oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives via one-pot coupling of hyrazine hydrate, ethyl cyanoacetate, malononitrile and aromatic aldehydes under reflux conditions in ethanol. Using this method we obtained low reaction times, easy isolation of the targeted molecules, e...
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 51 12 شماره
صفحات -
تاریخ انتشار 2015