Face selective reduction of the exocyclic double bond in isatin derived spirocyclic lactones.

نویسندگان

  • Sandeep Rana
  • Amarnath Natarajan
چکیده

We report an unusual face selective reduction of the exocyclic double bond in the α-methylene-γ-butyrolactone motif of spiro-oxindole systems. The spiro-oxindoles were assembled by an indium metal mediated Barbier-type reaction followed by an acid catalyzed lactonization.

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

Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams.

An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

متن کامل

Organocatalytic enantioselective and (Z)-selective allylation of 3-indolylmethanol via hydrogen-bond activation.

An organocatalytic asymmetric allylation of 3-indolylmethanol has been established via hydrogen-bond activating mode, which directly assembles isatin-derived 3-indolylmethanols and o-hydroxystyrenes into chiral allyl-substituted oxindoles with one all-carbon quaternary stereogenic center and one newly formed C=C bond in excellent enantioselectivity and (Z)-selectivity (up to 97% ee, >20 : 1 Z/E...

متن کامل

Natural Inhibitors of the Aromatase Enzyme*

The results of three years of search for natural aromatase inhibitors will be presented. Estrogen biosynthesis is catalyzed by the aromatase enzyme complex. This complex if made up of a member of the cytochrome P450 superfamily of enzymes known as cytochrome P450 aromatase (P450arom, produced by the CYP19 gene). Associated with this enzyme one finds the flavoprotein NADPH cytochrome P450 reduct...

متن کامل

Unique prototropy of meso-alkylidenyl carbaporphyrinoid possessing one meso-exocyclic double bond.

Generic synthesis, identification of structural identity, unique prototropy and spectroscopic properties of meso-alkylidenyl-thia(m-benzi)porphyrinoid containing one exocyclic double bond at the meso-position were presented.

متن کامل

Tandem au-catalyzed 3,3-rearrangement-[2 + 2] cycloadditions of propargylic esters: expeditious access to highly functionalized 2,3-indoline-fused cyclobutanes.

The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl(PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2,3-indoline and gamma-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and...

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:
  • Organic & biomolecular chemistry

دوره 11 2  شماره 

صفحات  -

تاریخ انتشار 2013