Enantioselective Synthesis of Aminoindan Carboxylic Acid Derivatives by the Catalytic Intramolecular [2+2+2] Cycloaddition of Amino-Acid-Tethered Triynes

Tahara, Y. k., Obinata, S., Kanyiva, K. S., Shibata, T., Mándi, A., Taniguchi, T., Monde, K.: Enantioselective Synthesis of Aminoindan Carboxylic Acid Derivatives by the Catalytic Intramolecular [2+2+2] Cycloaddition of Amino-Acid-Tethered Triynes.
Eur. J. Org. Chem. 2016 (7), 1405-1413, 2016.

doi DEA WoS Scopus

Journal metrics:

Q1 Organic Chemistry

Q1 Physical and Theoretical Chemistry

title:

Enantioselective Synthesis of Aminoindan Carboxylic Acid Derivatives by the Catalytic Intramolecular [2+2+2] Cycloaddition of Amino-Acid-Tethered Triynes

authors:

Tahara, Yu-ki
Obinata, Shuhei
Kanyiva, Kyalo Stephen
Shibata, Takanori
Mándi Attila
Taniguchi, Tohru
Monde, Kenji

published:

2016

type:

article

genre:

research article/review article

journal:

European Journal Of Organic Chemistry (ISSN: 1434-193X, 1099-0690)

language:

English

HAC:

Natural Sciences, Chemical Sciences

subjects:

Enantioselectivity, Cycloaddition, Rhodium, Amino acids

abstract:

The enantioselective synthesis of aminoindan carboxylic acid (Aic) derivatives was achieved by Rh-catalyzed intramolecular [2+2+2] cycloaddition of amino-acid-tethered triynes. This reaction, along with recrystallization, gave chiral tethered Aic derivatives with excellent enantiomeric excess. Subsequent hydrolysis of the tethered Aic compounds afforded chiral Aic derivatives, which were further transformed into a free Aic and its dimethyl ester in good yields.