Enantioselective transformation of Na2SO3 into allylic sulfonic acids under Pd catalysis.

نویسندگان

  • Wei Liu
  • Xiao-ming Zhao
  • Hong-bo Zhang
  • Liang Zhang
چکیده

Pd-catalyzed asymmetric allylic sulfonation of di-aryl-substituted allylic acetates with sodium sulfite (Na2SO3) in THF-H2O at room temperature was described. This method directly provided allylic sulfonic acids in up to excellent yield and enantioselectivity.

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

Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement

A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammo...

متن کامل

Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A.

Enantioselective Pd-catalyzed allylic alkylations of dihydropyrido[1,2-a]indolone (DHPI) substrates were used to construct the C20-quaternary stereocenters of multiple monoterpene indole alkaloids. Stereodivergent Pictet-Spengler and Bischler-Napieralski cyclization/reduction cascades furnish the cis- and trans-fused azadecalin subunits present in Aspidosperma and Kopsia alkaloids, respectively...

متن کامل

Pd(II)/Brønsted acid catalyzed enantioselective allylic C-H activation for the synthesis of spirocyclic rings.

A Pd(II)/Brønsted acid catalyzed migratory ring expansion for the synthesis of indene derivatives possessing a stereogenic spirocyclic carbon center was developed. This transformation is believed to mechanistically proceed via enantioselective allylic C-H activation with concomitant semipinacol ring expansion to the nascent π-allylpalladium species. Enantioselectivities as high as 98% ee were a...

متن کامل

Catalytic enantioselective addition of sodium bisulfite to chalcones.

Herein we report the first example of the catalytic enantioselective addition of sodium bisulfite to a,b-unsaturated alkenes 1a–q which was achieved by the selection of an appropriate aminothiourea bifunctional catalyst (Scheme 1). Following the pioneering work carried out by the groups of Soo s, Connon, Deng, and Wang, bifunctional catalysis has matured to become a prominent area of organic sy...

متن کامل

Construction of vicinal tertiary and all-carbon quaternary stereocenters via Ir-catalyzed regio-, diastereo-, and enantioselective allylic alkylation and applications in sequential Pd catalysis.

Highly congested vicinal stereocenters comprised of tertiary and all-carbon quaternary centers were generated via Ir-catalyzed asymmetric allylic alkylation of β-ketoesters. These catalytic reactions proceed in excellent yields with a broad scope on either reaction partner and with outstanding regio-, diastereo-, and enantiocontrol. Implementation of a subsequent Pd-catalyzed alkylation affords...

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 51 4  شماره 

صفحات  -

تاریخ انتشار 2015