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

Yu Ki Tahara; Shuhei Obinata; Kyalo Stephen Kanyiva; Takanori Shibata; Attila Mándi; Tohru Taniguchi; Kenji Monde

doi:10.1002/ejoc.201501612

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

Yu Ki Tahara, Shuhei Obinata, Kyalo Stephen Kanyiva, Takanori Shibata^*, Attila Mándi, Tohru Taniguchi, Kenji Monde

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1405-1413
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	7
DOIs	https://doi.org/10.1002/ejoc.201501612
Publication status	Published - 2016 Mar 1

Keywords

Amino acids
Cycloaddition
Enantioselectivity
Rhodium

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201501612

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Enantioselective Synthesis of Aminoindan Carboxylic Acid Derivatives by the Catalytic Intramolecular [2+2+2] Cycloaddition of Amino-Acid-Tethered Triynes. / Tahara, Yu Ki; Obinata, Shuhei; Kanyiva, Kyalo Stephen et al.

In: European Journal of Organic Chemistry, Vol. 2016, No. 7, 01.03.2016, p. 1405-1413.

Research output: Contribution to journal › Article › peer-review

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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.",

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AU - Obinata, Shuhei

AU - Kanyiva, Kyalo Stephen

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AU - Monde, Kenji

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KW - Cycloaddition

KW - Enantioselectivity

KW - Rhodium

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

Abstract

Keywords

ASJC Scopus subject areas

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