Diastereoselective synthesis and spin-dependent photodecarbonylation of di(3-phenyl-2-pyrrolidinon-3-yl)ketones: synthesis of nonadjacent and adjacent stereogenic quaternary centers.

نویسندگان

  • Marino J E Resendiz
  • Arunkumar Natarajan
  • Miguel A Garcia-Garibay
چکیده

A diastereoselective procedure to obtain N-para-methoxybenzyl bis-alpha,alpha'-3-(3-phenyl-2-pyrrolidinone)yl substituted ketones with non-adjacent quaternary stereocenters, DL-2 and meso-3 was followed by a photoinduced, spin-dependent, and diastereoselective decarbonylation to give compounds DL-4 and meso-5, with adjacent all-carbon quaternary stereogenic centers.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Total synthesis of (+/-)-herbertenolide by stereospecific formation of vicinal quaternary centers in a crystalline ketone.

[reaction: see text] The sesquiterpene (+/-)-herbertenolide was synthesized in seven steps from commercial 2-bromo-4-methylanisole. In the key step, two adjacent stereogenic quaternary centers were controlled by a highly chemoselective and stereospecific photodecarbonylation reaction of crystalline methyl-trans-3-(2-methyl-5-methoxyphenyl)-1,3-dimethyl-2-oxocyclohexancarboxylate (3). An efficie...

متن کامل

Green and diastereoselective synthesis of trans-3-(5-methylisoxazol-3-yl)-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazines

Reaction between aromatic aldehydes and 3–methyl-1-phenyl-2-pyrazoline-5-one catalyzed by nano-SiO2/HClO4 in water under reflux provided a simple and efficient route for the synthesis of 4-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(aryl)methyl)-3-methyl-1-phenyl-1H-pyrazol-5-ol derivatives in high yields.

متن کامل

Asymmetric catalytic [4 + 1] annulations catalyzed by quinidine: enantioselective synthesis of multi-functionalized isoxazoline N-oxides.

A highly regio-, chemo-, diastereo- and enantioselective organocatalytic [4 + 1] annulation of 2-halo-1,3-dicarbonyl compounds with Morita-Baylis-Hillman adducts catalyzed by commercially available, low cost quinidine for the preparation of synthetically unique and medicinally multi-functionalized isoxazoline N-oxides with three stereogenic centers including adjacent quaternary and tertiary ste...

متن کامل

Green and diastereoselective synthesis of trans-3-(5-methylisoxazol-3-yl)-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazines

Reaction between aromatic aldehydes and 3–methyl-1-phenyl-2-pyrazoline-5-one catalyzed by nano-SiO2/HClO4 in water under reflux provided a simple and efficient route for the synthesis of 4-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(aryl)methyl)-3-methyl-1-phenyl-1H-pyrazol-5-ol derivatives in high yields.

متن کامل

Highly diastereoselective and enantiospecific allylation of ketones and imines using borinic esters: contiguous quaternary stereogenic centers.

3,3-Disubstituted allylic boronic esters are not sufficiently reactive to react with ketones and imines. However, they can be converted into the corresponding borinic esters by the sequential addition of nBuLi and TFAA. These reactive intermediates possess the perfect balance between reactivity and configurational stability. Their enhanced reactivity allows the highly selective allylation of bo...

متن کامل

ذخیره 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 نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Chemical communications

دوره 2  شماره 

صفحات  -

تاریخ انتشار 2008