Deciphering DNA-based asymmetric catalysis through intramolecular Friedel-Crafts alkylations.

نویسندگان

  • Soyoung Park
  • Keiichi Ikehata
  • Ryo Watabe
  • Yuta Hidaka
  • Arivazhagan Rajendran
  • Hiroshi Sugiyama
چکیده

We describe asymmetric intramolecular Friedel-Crafts alkylations with a DNA-based hybrid catalyst and propose a plausible binding model. This study shows promise for studying relationships between the helical chirality of DNA and enantioselectivity of the chemical reaction.

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

Organic co-solvents in aqueous DNA-based asymmetric catalysis.

Water-miscible organic co-solvents can be used in DNA-based catalytic asymmetric reactions at appreciable concentration without a negative effect on enantioselectivity. While the rate of the copper(II) Diels-Alder reaction is affected negatively by the presence of organic co-solvents, the copper(II) catalyzed Michael addition and Friedel-Crafts alkylation reaction are significantly faster. Addi...

متن کامل

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

The development of efficient Friedel-Crafts alkylations of arenes and heteroarenes using only catalytic amounts of a Lewis acid has gained much attention over the last decade. The new catalytic approaches described in this review are favoured over classical Friedel-Crafts conditions as benzyl-, propargyl- and allyl alcohols, or styrenes, can be used instead of toxic benzyl halides. Additionally...

متن کامل

Construction of Furan Derivatives with a Trifluoromethyl Stereogenic Center: Enantioselective Friedel-Crafts Alkylations via Formal Trienamine Catalysis.

An asymmetric Friedel-Crafts alkylation reaction of 2-furfuryl ketones with β-trifluoromethyl enones has been developed via formal trienamine catalysis of a bifunctional primary amine-thiourea substance derived from L-tert-leucine, delivering the furan derivatives incorporating a stereogenic trifluoromethyl (CF3) group in good to high yields with excellent enantioselectivity.

متن کامل

DNA-cellulose: an economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis.

The challenge in DNA-based asymmetric catalysis is to perform a reaction in the vicinity of the helix by incorporating a small-molecule catalyst anchored to the DNA in a covalent, dative, or non-covalent yet stable fashion in order to ensure high levels of enantio-discrimination. Here, we report the first generation of a DNA-based catalyst bound to a cellulose matrix. The chiral biomaterial is ...

متن کامل

Organocatalytic vinyl and Friedel-Crafts alkylations with trifluoroborate salts.

Over the last 8 years, our laboratory has developed the concept of iminium catalysis, a mode of LUMO-lowering activation that has enabled the invention of a large number of enantioselective organocatalytic transformations including Diels-Alder cycloadditions, Friedel-Crafts alkylations, Mukaiyama-Michael additions, hydrogenations, and heteroconjugate additions.1 Central to the utility of this t...

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:
  • Chemical communications

دوره 48 84  شماره 

صفحات  -

تاریخ انتشار 2012