Biocatalysed concurrent production of enantioenriched compounds through parallel interconnected kinetic asymmetric transformations.

نویسندگان

  • Ana Rioz-Martínez
  • Fabricio R Bisogno
  • Cristina Rodríguez
  • Gonzalo de Gonzalo
  • Iván Lavandera
  • Daniel E Torres Pazmiño
  • Marco W Fraaije
  • Vicente Gotor
چکیده

Parallel interconnected kinetic asymmetric transformations were performed in order to obtain enantioenriched derivatives starting from a set of racemic or prochiral compounds. Thus, in a one-pot reaction using two redox biocatalysts (a BVMO and an ADH) and a catalytic amount of cofactor that acts as a mediator, enantioenriched ketones, sulfoxides, and sec-alcohols were concurrently obtained in a strict parallel way, minimising the quantity of reagents employed. By selecting the appropriate biocatalysts, this methodology represents a potential tool for performing stereodivergent transformations.

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

Chemoenzymatic Resolution in Dynamic Systems: Screening, Classification and Asymmetric Synthesis

This thesis is divided into four parts, all centered around Constitutional Dynamic Chemistry (CDC) and Dynamic Kinetic Resolution (DKR) using biocatalysts for selective transformations, and their applications in screening of bioactive compounds, organic synthesis, and enzyme classification. In part one, an introduction to CDC and DKR is presented, illustrating the basic concepts, practical cons...

متن کامل

Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters.

A highly enantioselective transformation catalyzed by chiral (acyclic diaminocarbene)gold(I) complexes is reported. The enantioselective synthesis of 2-substituted chromenyl pivalates from racemic phenol-substituted propargyl pivalates was developed. Rearrangement of the substrates in the presence of cationic gold gave allene intermediates, whose cyclization resulted in formation of enantioenri...

متن کامل

Organocatalytic asymmetric remote aziridination of 2,4-dienals.

Highly regio- and stereoselective remote aziridination of 2,4-dienals has been developed, based on a vinylogous iminium-ion-dienamine catalytic cascade reaction. Transformations of the aziridine products into enantioenriched motifs are also demonstrated. Furthermore, the reaction concept is extended to include enantioselective 1,6-addition of thiols.

متن کامل

Synthesis of (-)-octalactin a by a strategic vanadium-catalyzed oxidative kinetic resolution.

The kinetic resolution of racemic material is a well-established approach used to prepare a wide range of enantiomerically enriched compounds. However, the overall efficiency of a standard kinetic resolution is limited to a maximum theoretical yield of 50% of the enriched chiron, with the balance of undesired material being discarded in most applications. As a result of this inherent overall ef...

متن کامل

Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide-alkyne cycloadditions.

The synthesis and kinetic resolution of quaternary oxindoles through copper catalysed azide-alkyne cycloadditions is presented. Selectivity factors (s) up to 22.1 ± 0.5 are reported. Enantioenriched alkynes and triazoles were obtained in ≥80% enantiomeric excess (e.e.).

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 8 6  شماره 

صفحات  -

تاریخ انتشار 2010