𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Enzymes in Organic Synthesis, 18. Lipase-catalyzed Asymmetric Alcoholysis of 3-Substituted Pentanedioic Anhydrides

✍ Scribed by Ozegowski, Rüdiger ;Kunath, Annamarie ;Schick, Hans

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
474 KB
Volume
1993
Category
Article
ISSN
0947-3440

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The influence of several enzymes, alcohols, and solvents on the stereochemical outcome of the asymmetric alcoholysis of 3‐substituted pentanedioic anhydrides was investigated. The alcoholysis of 3‐acetoxypentanedioic anhydride (5a) in diethyl ether with 2‐methylpropanol afforded the (3__S__)‐monoester (S)‐6a with an enantiomeric excess of > 98% when the lipase from Candida sp. 382 was used as the enzyme. Under the same conditions, 3‐methoxypentanedioic anhydride (5c) was converted by the lipase of Pseudomonas cepacia (Amano PS) into the (3__R__)‐monoester (R)‐6c with an e.e. of 90%.

📜 SIMILAR VOLUMES

Enzymes in Organic Synthesis, 26. Synthe
Enzymes in Organic Synthesis, 26. Synthesis of Enantiomerically Enriched 2,3- and 3,4-Dimethylpentan-5-olides by Lipase-Catalyzed Regio- and Enantioselective Alcoholysis of cis- and trans-2,3-Dimethylpentanedioic Anhydrides
✍ Ozegowski, Rüdiger ;Kunath, Annamarie ;Schick, Hans 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 English ⚖ 680 KB

## Abstract The enzyme‐catalyzed regio‐ and enantioselective alcoholysis of racemic __cis__‐ and __trans__‐2,3‐dimethylpentanedioc anhydride in the presence of Novozym 435 from __Candida antarctica__ afforded two of the eight possible monoesters with an enantiomeric excess higher than 90%. Regiosel

Enzymes in organic synthesis, 25. Lipase
Enzymes in organic synthesis, 25. Lipase-catalyzed sequential esterification of (±)-2-methylbutanedioic anhydride — a biocatalytical access to an enantiomerically pure 1-monoester of (S)-2-methylbutanedioic acid
✍ Ozegowski, Rüdiger ;Kunath, Annamarie ;Schick, Hans 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 462 KB 👁 1 views

## Abstract The preparation of enantiomerically pure 1‐(2‐methylpropyl) 4‐hydrogen (__S__)‐2‐methylbutanedioate (__ent__‐3) by an enzyme‐catalyzed sequential esterification of (±)‐2‐methylbutanedioic anhydride (__rac__‐1) demands two different enzymes. Lipozyme, a lipase from __Mucor miehei__, was

Enzymes in organic synthesis, 21. Lipase
Enzymes in organic synthesis, 21. Lipase-catalyzed conversion of (±)-2-methylglutaric anhydride into (S)-2-methyl- and (R)-4-methyl-δ-valerolactone via a regio- and enantioselective sequential esterification
✍ Ozegowski, Rüdiger ;Kunath, Annamarie ;Schick, Hans 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 English ⚖ 500 KB

## Abstract The enzyme‐catalyzed sequential esterification of (±)‐2‐methylpentanedioic anhydride (__rac__‐1) with 2‐methylpropanol in diethyl ether afforded a 1:1 mixture of 1‐(2‐methylpropyl) 5‐hydrogen (__S__)‐4‐methylpentanedioate (__ent__‐2) with an enantiomeric excess of 88% and 1‐(2‐methylpro