Literature DB >> 26388298

From meso-Lactide to Isotactic Polylactide: Epimerization by B/N Lewis Pairs and Kinetic Resolution by Organic Catalysts.

Jian-Bo Zhu1, Eugene Y-X Chen1.   

Abstract

B/N Lewis pairs have been discovered to catalyze rapid epimerization of meso-lactide (LA) or LA diastereomers quantitatively into rac-LA. The obtained rac-LA is kinetically polymerized into poly(L-lactide) and optically resolved D-LA, with a high stereoselectivity k(L)/k(D) of 53 and an ee of 91% at 50.6% monomer conversion, by newly designed bifunctional chiral catalyst 4 that incorporates three key elements (β-isocupreidine core, thiourea functionality, and chiral BINAM) into a single organic molecule. The epimerization and enantioselective polymerization can be coupled into a one-pot process for transforming meso-LA directly into poly(L-lactide) and D-LA.

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Year:  2015        PMID： 26388298     DOI： 10.1021/jacs.5b08658

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Stereoselective photoredox ring-opening polymerization of O-carboxyanhydrides.

Authors:  Quanyou Feng; Lei Yang; Yongliang Zhong; Dong Guo; Guoliang Liu; Linghai Xie; Wei Huang; Rong Tong
Journal:  Nat Commun       Date:  2018-04-19       Impact factor: 14.919

2.  Controlled and Efficient Polymerization of Conjugated Polar Alkenes by Lewis Pairs Based on Sterically Hindered Aryloxide-Substituted Alkylaluminumitle.

Authors:  Xiaojun Wang; Yixin Zhang; Miao Hong
Journal:  Molecules       Date:  2018-02-17       Impact factor: 4.411

3.  Isoselective Lactide Ring Opening Polymerisation using [2]Rotaxane Catalysts.

Authors:  Jason Y C Lim; Nattawut Yuntawattana; Paul D Beer; Charlotte K Williams
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-28       Impact factor: 15.336

Review 4.  Spotting Trends in Organocatalyzed and Other Organomediated (De)polymerizations and Polymer Functionalizations.

Authors:  María Valle; Marta Ximenis; Xabier Lopez de Pariza; Julian M W Chan; Haritz Sardon
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-10       Impact factor: 16.823

5.  "Like Recycles Like": Selective Ring-Closing Depolymerization of Poly(L-Lactic Acid) to L-Lactide.

Authors:  Linnea Cederholm; Jakob Wohlert; Peter Olsén; Minna Hakkarainen; Karin Odelius
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-09       Impact factor: 16.823

6.  Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3-Isothiocyanato Oxindoles with Dibenzylidene Ketones.

Authors:  Dan Du; Yu Jiang; Qin Xu; Xiao-Ge Li; Min Shi
Journal:  ChemistryOpen       Date:  2016-05-25       Impact factor: 2.911

7.  Zn(OAc)₂-Catalyzing Ring-Opening Polymerization of N-Carboxyanhydrides for the Synthesis of Well-Defined Polypeptides.

Authors:  Yanzhao Nie; Xinmei Zhi; Haifeng Du; Jing Yang
Journal:  Molecules       Date:  2018-03-26       Impact factor: 4.411

Review 8.  Lewis Pair Catalysts in the Polymerization of Lactide and Related Cyclic Esters.

Authors:  Xinlei Li; Changjuan Chen; Jincai Wu
Journal:  Molecules       Date:  2018-01-17       Impact factor: 4.411

9.  Facile Preparation of Stereoblock PLA From Ring-Opening Polymerization of rac-Lactide by a Synergetic Binary Catalytic System Containing Ureas and Alkoxides.

Authors:  Ze Kan; Wenlong Luo; Tong Shi; Chuanzhi Wei; Binghao Han; Dejuan Zheng; Shaofeng Liu
Journal:  Front Chem       Date:  2018-11-09       Impact factor: 5.221

10.  Highly Efficient One-Pot Synthesis of COS-Based Block Copolymers by Using Organic Lewis Pairs.

Authors:  Jia-Liang Yang; Xiao-Han Cao; Cheng-Jian Zhang; Hai-Lin Wu; Xing-Hong Zhang
Journal:  Molecules       Date:  2018-01-31       Impact factor: 4.411
  10 in total

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