Asymmetric syntheses of epohelmins A and B by In-mediated allylation.

نویسندگان

  • Yi-Wen Liu
  • Pan Han
  • Wen Zhou
  • Zhuo-Ya Mao
  • Chang-Mei Si
  • Bang-Guo Wei
چکیده

A diastereoselective new approach for the synthesis of trans-4-hydroxy-5-allyl-2-pyrrolidinone 9 has been developed through In-mediated allylation of α-chiral aldimine 8 with allyl bromide. The stereochemistry at the C-2 stereogenic center of 9 was controlled by both the α-OTBS substitution and the sulfinamide moiety. The utility of this asymmetric allylation is demonstrated by the asymmetric syntheses of epohelmins A (4) and B (10).

برای دانلود رایگان 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

A general enantioselective route to the chamigrene natural product family.

Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy...

متن کامل

General and practical approach to the syntheses of linear homoallylic alcohols*

We have demonstrated that metal-mediated allylation of aldehydes can afford γ-homoallylic alcohols or α-linear homoallylic alcohols by judicious choice of the solvents. A new mechanism has been proposed to account for this new α-selective metal-mediated allylation reaction. On the other hand, the metal-mediated prenylation under the same conditions to obtain α-prenyl alcohols was unsuccessful. ...

متن کامل

Diastereoselective indium-mediated allylation of N-tert-butanesulfinyl ketimines: easy access to asymmetric quaternary stereocenters bearing nitrogen atoms.

Indium-mediated allylation of N-tert-butanesulfinyl ketimines afforded in high yields and diastereoselectivities homoallylic amine derivatives with the nitrogen atom bonded to a quaternary stereocenter.

متن کامل

Zn-mediated asymmetric allylation of N-tert-butanesulfinyl ketimines: an efficient and practical access to chiral quaternary 3-aminooxindoles.

Room temperature zinc-mediated diastereoselective allylation or propargylation of isatin-derived N-tert-butanesulfinyl ketimines for synthesis of highly enantiomerically enriched tetrasubstituted 3-aminooxindoles is described.

متن کامل

Quantum chemical study on asymmetric allylation of benzaldehyde in the presence of chiral allylboronate.

The quantum chemical method is employed to study the modified asymmetric allylation of benzaldehyde controlled by diisopropyl D-(-)-tartrate auxiliary. All the structures are optimized completely at the B3LYP/6-31G(d,p) level. The (R)-secondary alcohol can be achieved mainly through a six-membered ring chair-like transition state structure. From the relative reaction rates theory the main produ...

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

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 14 45  شماره 

صفحات  -

تاریخ انتشار 2016