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Literature DB >> 25339781

Investigations Concerning the Syntheses of TADDOL-Derived Secondary Amines and Their Use To Access Novel Chiral Organocatalysts.

Abstract

A structurally carefully diversified library of novel TADDOL-derived chiral secondary amines was synthesized and investigated for their applicability to obtain new organocatalysts like chiral Lewis bases and chiral phase-transfer catalysts. The scope and limitations of the developed syntheses routes to access these catalysts as well their catalytic performance in different benchmark reactions were systematically investigated. The most powerful of the catalysts prepared was found to be highly useful for the phase-transfer catalyzed α-alkylation of glycine Schiff base (high yields and up to 93% ee).

Entities: Chemical

Keywords: Lewis base catalysis; asymmetric alkylation; asymmetric phase-transfer catalysis; chiral pool; tartaric acid

Year: 2012 PMID： 25339781 PMCID： PMC4202115 DOI： 10.1055/s-0032-1316804

Source DB: PubMed Journal: Synthesis (Stuttg) ISSN： 0039-7881 Impact factor: 3.157

24 in total

1. Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation.

Authors: Takashi Ohshima; Vijay Gnanadesikan; Tomoyuki Shibuguchi; Yuhei Fukuta; Tetsuhiro Nemoto; Masakatsu Shibasaki
Journal: J Am Chem Soc Date: 2003-09-17 Impact factor: 15.419

2. Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine schiff base using a chiral two-center phase-transfer catalyst.

Authors: Akihiro Okada; Tomoyuki Shibuguchi; Takashi Ohshima; Hyuma Masu; Kentaro Yamaguchi; Masakatsu Shibasaki
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

3. Catalytic asymmetric syntheses of isoxazoline-N-oxides under phase-transfer conditions.

Authors: Taichi Kano; Akihiro Yamamoto; Sunhwa Song; Keiji Maruoka
Journal: Chem Commun (Camb) Date: 2011-02-01 Impact factor: 6.222

4. Enantioselective [1,2]-Stevens rearrangement of quaternary ammonium salts. A mechanistic evaluation.

Authors: Maria-Héléna Gonçalves-Farbos; Laurent Vial; Jérôme Lacour
Journal: Chem Commun (Camb) Date: 2007-12-21 Impact factor: 6.222

Review 5. Recent development and application of chiral phase-transfer catalysts.

Authors: Takuya Hashimoto; Keiji Maruoka
Journal: Chem Rev Date: 2007-12 Impact factor: 60.622

6. Catalytic asymmetric synthesis of axially chiral o-iodoanilides by phase-transfer catalyzed alkylations.

Authors: Seiji Shirakawa; Kun Liu; Keiji Maruoka
Journal: J Am Chem Soc Date: 2011-12-30 Impact factor: 15.419

7. Asymmetric PTC C-alkylation catalyzed by chiral derivatives of tartaric acid and aminophenols. Synthesis Of (R)- and (S)-alpha-methyl amino acids

Authors:
Journal: J Org Chem Date: 2000-10-20 Impact factor: 4.354

8. The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters.

Authors: Martin J O'Donnell
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

9. Catalytic asymmetric phase-transfer Michael reaction and Mannich-type reaction of glycine Schiff bases with tartrate-derived diammonium salts.

Authors: Tomoyuki Shibuguchi; Hisashi Mihara; Akiyoshi Kuramochi; Takashi Ohshima; Masakatsu Shibasaki
Journal: Chem Asian J Date: 2007-06-04

7. Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts.

Authors: Lei Jin; Shuai Zhao; Xin Chen
Journal: Molecules Date: 2018-06-12 Impact factor: 4.411

8. Towards Tartaric-Acid-Derived Asymmetric Organocatalysts.

Authors: Katharina Gratzer; Guddeangadi N Gururaja; Mario Waser
Journal: European J Org Chem Date: 2013-06-03

8 in total

Investigations Concerning the Syntheses of TADDOL-Derived Secondary Amines and Their Use To Access Novel Chiral Organocatalysts.

1. Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation.

2. Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine schiff base using a chiral two-center phase-transfer catalyst.

3. Catalytic asymmetric syntheses of isoxazoline-N-oxides under phase-transfer conditions.

4. Enantioselective [1,2]-Stevens rearrangement of quaternary ammonium salts. A mechanistic evaluation.

Review 5. Recent development and application of chiral phase-transfer catalysts.

6. Catalytic asymmetric synthesis of axially chiral o-iodoanilides by phase-transfer catalyzed alkylations.

7. Asymmetric PTC C-alkylation catalyzed by chiral derivatives of tartaric acid and aminophenols. Synthesis Of (R)- and (S)-alpha-methyl amino acids

8. The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters.

9. Catalytic asymmetric phase-transfer Michael reaction and Mannich-type reaction of glycine Schiff bases with tartrate-derived diammonium salts.

10. A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions.

1. Asymmetric cyclopropanation of chalcones using chiral phase-transfer catalysts.

2. Towards an asymmetric organocatalytic α-cyanation of β-ketoesters.

3. Syntheses and Applications of (Thio)Urea-Containing Chiral Quaternary Ammonium Salt Catalysts.

4. Asymmetric phase-transfer catalysed β-addition of isoxazolidin-5-ones to MBH carbonates.

5. Application scope and limitations of TADDOL-derived chiral ammonium salt phase-transfer catalysts.

Review 6. Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

7. Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts.

8. Towards Tartaric-Acid-Derived Asymmetric Organocatalysts.