Samarium(ii) iodide-mediated intramolecular pinacol coupling reactions with cyclopropyl ketones.
نویسندگان
چکیده
The first reported intramolecular pinacol coupling of cyclopropyl ketones has been achieved, demonstrating that cyclisation competes favourably with ring-opening of the cyclopropyl ketyl radical.
منابع مشابه
Ketone-imide versus ketone-oxime reductive cross-coupling promoted by samarium diiodide: new mechanistic insight gained from a failed aminocyclopentitol synthesis.
[reaction: see text] The intramolecular 1,6-ketone/imide reductive coupling promoted by samarium diiodide competes favorably with an alternative 1,5-ketone/oxime ether coupling in a keto-oxime substrate derived from D-glucosamine N-protected with a phthalimido group. This pinacol coupling reaction affords new homochiral alpha-hydroxylactam scaffolds that could be useful in diversity-oriented sy...
متن کاملCyclizations producing hydrindanones with two methyl groups at the juncture positions mediated by samarium diiodide and electrolysis.
One-electron reductive intramolecular cyclization of enones with ketones or aldehydes mediated by samarium diiodide and electrolysis to afford cis-trimethyl- hydrindanolones. The reactions gave selectivities ranging from 1:1 to 100:0 depending on the conditions.
متن کاملIntramolecular Reductive Coupling of Carbonyl-Tethered Oxime Ethers Promoted by Samarium Diiodide: A Powerful Method for the Stereoselective Synthesis of Aminocyclopentitols+**
There is a growing interest in the synthesis of stereochemically pure aminocyclopentitols as key intermediates for the preparation of carbocyclic glycosidase inhibitors,I carbocyclic nucleosides,2 and analogues. To this end, a series of carbocyclization strategies have been developed, a particularly interesting process being the intramolecular trapping of a radical by an oxime ethel3 or by a hy...
متن کاملPinacol coupling of aromatic aldehydes and ketones mediated by TiCl4-Zn in ethyl acetate under ultrasound
The reductive coupling of aldehydes and ketones to give diols is a powerful method for constructing vicinal functional carbon-carbon bonds, which has been employed successfully in synthesis of many natural products and asymmetric ligands. In the past years, various metal reagents and their complexes have been tried for mediating pinacol coupling reactions, such as Mg, Mn, Al, In, SmI2, Zn, CpV(...
متن کاملDirect reductive coupling of secondary amides: chemoselective formation of vicinal diamines and vicinal amino alcohols.
We report the first one-pot reductive homocoupling reaction of secondary amides and cross-coupling reaction of secondary amides with ketones to give secondary vicinal diamines and amino alcohols. This method relies on the direct generation of α-amino carbon radicals from secondary amides by activation with trifluoromethanesulfonic anhydride, partial reduction with triethylsilane and samarium di...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical communications
دوره 45 شماره
صفحات -
تاریخ انتشار 2007