Convenient enantioselective preparation of salsolinol-1-carboxylic acid

Masao Kawai; Yulin Deng; Ikuko Kimura; Hatsuo Yamamura; Shuki Araki; Makoto Naoi

doi:10.1016/S0957-4166(97)00149-3

Convenient enantioselective preparation of salsolinol-1-carboxylic acid

Masao Kawai^*, Yulin Deng, Ikuko Kimura, Hatsuo Yamamura, Shuki Araki, Makoto Naoi

^*Corresponding author for this work

Nagoya Institute of Technology

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

17 Citations (Scopus)

Abstract

Pictet-Spengler condensation of dopamine with (+)-menthyl pyruvate afforded a diastereomeric mixture of menthyl salsolinol-1-carboxylate, from which pure diastereomer was isolated by repeated recrystallizations in ca. 20% yield. Acid hydrolysis of the menthyl ester furnished (-)-(R)-salsolinol-1-carboxylic acid in good yield.

Original language	English
Pages (from-to)	1487-1490
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	8
Issue number	9
DOIs	https://doi.org/10.1016/S0957-4166(97)00149-3
Publication status	Published - 8 May 1997
Externally published	Yes

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Kawai, M., Deng, Y., Kimura, I., Yamamura, H., Araki, S., & Naoi, M. (1997). Convenient enantioselective preparation of salsolinol-1-carboxylic acid. Tetrahedron Asymmetry, 8(9), 1487-1490. https://doi.org/10.1016/S0957-4166(97)00149-3

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abstract = "Pictet-Spengler condensation of dopamine with (+)-menthyl pyruvate afforded a diastereomeric mixture of menthyl salsolinol-1-carboxylate, from which pure diastereomer was isolated by repeated recrystallizations in ca. 20% yield. Acid hydrolysis of the menthyl ester furnished (-)-(R)-salsolinol-1-carboxylic acid in good yield.",

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AU - Kawai, Masao

AU - Deng, Yulin

AU - Kimura, Ikuko

AU - Yamamura, Hatsuo

AU - Araki, Shuki

AU - Naoi, Makoto

PY - 1997/5/8

Y1 - 1997/5/8

N2 - Pictet-Spengler condensation of dopamine with (+)-menthyl pyruvate afforded a diastereomeric mixture of menthyl salsolinol-1-carboxylate, from which pure diastereomer was isolated by repeated recrystallizations in ca. 20% yield. Acid hydrolysis of the menthyl ester furnished (-)-(R)-salsolinol-1-carboxylic acid in good yield.

AB - Pictet-Spengler condensation of dopamine with (+)-menthyl pyruvate afforded a diastereomeric mixture of menthyl salsolinol-1-carboxylate, from which pure diastereomer was isolated by repeated recrystallizations in ca. 20% yield. Acid hydrolysis of the menthyl ester furnished (-)-(R)-salsolinol-1-carboxylic acid in good yield.

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DO - 10.1016/S0957-4166(97)00149-3

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JF - Tetrahedron Asymmetry

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ER -

Convenient enantioselective preparation of salsolinol-1-carboxylic acid

Abstract

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