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

Access to Document

10.1016/S0957-4166(97)00149-3

Cite this

@article{e3e7bcd3d3204220bed042614a588ff5,

title = "Convenient enantioselective preparation of salsolinol-1-carboxylic acid",

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.",

author = "Masao Kawai and Yulin Deng and Ikuko Kimura and Hatsuo Yamamura and Shuki Araki and Makoto Naoi",

year = "1997",

month = may,

day = "8",

doi = "10.1016/S0957-4166(97)00149-3",

language = "English",

volume = "8",

pages = "1487--1490",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Ltd.",

number = "9",

}

TY - JOUR

T1 - Convenient enantioselective preparation of salsolinol-1-carboxylic acid

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.

UR - http://www.scopus.com/inward/record.url?scp=0030970535&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(97)00149-3

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

M3 - Article

AN - SCOPUS:0030970535

SN - 0957-4166

VL - 8

SP - 1487

EP - 1490

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 9

ER -

Convenient enantioselective preparation of salsolinol-1-carboxylic acid

Abstract

Access to Document

Other files and links

Fingerprint

Cite this