Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine.

Literature DB >> 15901190

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine.

Gang Chen¹, Norihito Tokunaga, Tamio Hayashi.

Abstract

[reaction: see text]. Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins proceeded with high enantioselectivity in the presence of a rhodium catalyst (3 mol %) generated from Rh(acac)(C2H4)2 and (R)-Segphos to give the corresponding (R)-4-arylchroman-2-ones in over 99% ee. This asymmetric reaction was applied to the synthesis of (R)-tolterodine.

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 15901190 DOI： 10.1021/ol0507367

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

Keyword Cloud
Cited

9 in total

1. Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones.

Authors: Christian A Malapit; Irungu K Luvaga; Donald R Caldwell; Nicholas K Schipper; Amy R Howell
Journal: Org Lett Date: 2017-08-15 Impact factor: 6.005

2. Anionic four-electron donor-based palladacycles as catalysts for addition reactions of arylboronic acids with alpha,beta-unsaturated ketones, aldehydes, and alpha-ketoesters.

Authors: Ping He; Yong Lu; Cheng-Guo Dong; Qiao-Sheng Hu
Journal: Org Lett Date: 2007-01-18 Impact factor: 6.005

3. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors: Anna Lee; Karl A Scheidt
Journal: Chem Commun (Camb) Date: 2015-02-25 Impact factor: 6.222

8. Efficient kinetic resolution in the asymmetric transfer hydrogenation of 3-aryl-indanones: applications to a short synthesis of (+)-indatraline and a formal synthesis of (R)-tolterodine.

Authors: Songsoon Park; Hyeon-Kyu Lee
Journal: RSC Adv Date: 2021-06-30 Impact factor: 3.361

9. Chiral Fe(ii) complex catalyzed enantioselective [1,3] O-to-C rearrangement of alkyl vinyl ethers and synthesis of chromanols and beyond.

Authors: Lifeng Wang; Pengfei Zhou; Qianchi Lin; Shunxi Dong; Xiaohua Liu; Xiaoming Feng
Journal: Chem Sci Date: 2020-09-07 Impact factor: 9.825

9 in total

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine.

1. Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones.

2. Anionic four-electron donor-based palladacycles as catalysts for addition reactions of arylboronic acids with alpha,beta-unsaturated ketones, aldehydes, and alpha-ketoesters.

3. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

4. Enantioselective synthesis of (R)-tolterodine using lithiation/borylation-protodeboronation methodology.

5. Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles.

6. A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates.

7. On the Absolute Stereochemistry of Tolterodine: A Circular Dichroism Study.

8. Efficient kinetic resolution in the asymmetric transfer hydrogenation of 3-aryl-indanones: applications to a short synthesis of (+)-indatraline and a formal synthesis of (R)-tolterodine.

9. Chiral Fe(ii) complex catalyzed enantioselective [1,3] O-to-C rearrangement of alkyl vinyl ethers and synthesis of chromanols and beyond.