Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis

نویسندگان

  • Yan Zhang
  • Pornrapee Vongvilai
  • Morakot Sakulsombat
  • Andreas Fischer
  • Olof Ramström
چکیده

Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

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

Dynamic Covalent Resolution: Applications for System Screening and Asymmetric Synthesis

Combined thermodynamic/kinetic events amount to a kinetically controlled Dynamic Combinatorial Resolution (DCR) process, where the lability of the molecules/aggregates are used to generate dynamics, and the species experiencing the lowest activation energy is selected via kinetic process. Both interand intramolecular processes can be performed using this concept, resulting in complete resolutio...

متن کامل

Lipase-catalyzed asymmetric synthesis of oxathiazinanones through dynamic covalent kinetic resolution.

A domino addition-lactonization pathway has been applied to a dynamic covalent resolution protocol, leading to efficient oxathiazinanone formation as well as chiral discrimination. A new, double biocatalytic pathway has furthermore been proposed and evaluated where the initial product inhibition could be efficiently circumvented.

متن کامل

Organocatalytic diastereoselective synthesis of chiral decalines through the domino Claisen-Schmidt/Henry reaction.

General and operative domino Claisen-Schmidt/Henry (CS/H) reaction has been revealed to obtain highly substituted chiral decalines in good yields with excellent ees and des by using push-pull enamine catalysis.

متن کامل

Dioxindole in asymmetric catalytic synthesis: direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes.

The asymmetric Michael addition of dioxindoles to β-substituted nitroalkenes is reported. The bifunctional primary amine-thiourea A, by means of a non-covalent-based mode of catalysis, secures direct access to 3-substituted 3-hydroxyoxindole derivatives with high stereocontrol.

متن کامل

[Development of novel asymmetric reactions oriented to next-generation enzymatic organic syntheses].

Enzyme-catalyzed organic syntheses have enormous potential in the development of environmentally benign processes. In the last two decades, increased efforts have been devoted to making this a reality. However, the utility of the enzymes is generally limited. For example, although the lipases are extensively used for the kinetic resolution or the desymmetrization of alcohols and carboxylic acid...

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:

دوره 356  شماره 

صفحات  -

تاریخ انتشار 2014