Chemo-, regio- and stereoselective preparation of silyl enol ethers from thiol esters and bis(iodozincio)alkane.

نویسندگان

  • Akihiro Ooguri
  • Zenichi Ikeda
  • Seijiro Matsubara
چکیده

Treatment of thiol ester with bis(iodozincio)alkane in the presence of palladium catalyst followed by silylation affords Z-silyl enol ether chemo-, regio- and stereoselectively.

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

Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate th...

متن کامل

Nitrile assisted, Brønsted acid catalyzed regio and stereoselective diarylphosphonylation of allyl silyl ethers.

We have discovered a mild, catalytic protocol for the regio- and stereoselective synthesis of trisubstituted allyl diarylphosphonates from the corresponding disubstituted allyl silyl ethers, circumventing the challenges related to the preparation and availability of stereodefined trisubstituted olefins. A closely related arylation reaction was also discovered during the methodology development....

متن کامل

The stereoselective synthesis of α-amino aldols starting from terminal alkynes.

A new procedure for the stereoselective synthesis of syn α-amino β-oxy ketones is reported. It consists of two steps; in the first step, α-amino silyl enol ethers having a (Z) geometry are prepared from 1-alkynes via 1-sulfonyl-1,2,3-triazoles. In the second step, the silyl enol ethers undergo the TiCl4-mediated Mukaiyama aldol reaction with aldehydes to produce α-amino β-oxy ketones with excel...

متن کامل

A highly diastereoselective “super silyl” governed aldol reaction: synthesis of α,β-dioxyaldehydes and 1,2,3-triols

A highly diastereoselective approach for the synthesis of protected a,b-dioxyaldehydes derived from (Z)tris(trimethylsilyl)silyl “super silyl” enol ethers is described. A general and highly syn-stereoselective aldol reaction directed by the “super silyl” group catalyzed by triflimide (HNTf2) is developed providing a,bdioxyaldehydes and 1,2,3-triol fragments which can be a useful platform for th...

متن کامل

Palladium-catalyzed haloallylation of aromatic ynol ethers with allyl chlorides: a highly regio- and stereoselective approach to (1E)-α-chloroenol ethers.

Described herein is a Pd-catalyzed haloallylation of aromatic ynol ethers and allyl chlorides, allowing facile access to (1E)-α-chloroenol ethers in a highly regio- and stereoselective manner. The synthetic utility of this method is demonstrated well by the synthesis of the stereodefined multisubstituted enol ethers and α-allylated carbonyl compounds.

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 45  شماره 

صفحات  -

تاریخ انتشار 2007