Asymmetric pictet-spengler reactions: Synthesis of 1,2,3,4-tetrahydroisoquinoline carboxylic acid (Tic) chimeras

J. Spengler; H. Schedel; J. Sieler; P. J.L.M. Quaedflieg; Q. B. Broxterman; A. L.L. Duchateau; K. Burger

doi:10.1055/s-2001-16091

Asymmetric pictet-spengler reactions: Synthesis of 1,2,3,4-tetrahydroisoquinoline carboxylic acid (Tic) chimeras

J. Spengler
, H. Schedel
, J. Sieler
, P. J.L.M. Quaedflieg
, Q. B. Broxterman
, A. L.L. Duchateau
, K. Burger

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

20 Scopus citations

Abstract

A preparatively simple diastereoselective synthesis of the amino acid chimera (1S,3S)-1,2,3,4-tetrahydroisoquinoline-1,3-dicarboxylic acid from hexafluoroacetone-protected phenylalanine and glyoxylic acid hydrate via Pictet-Spengler reaction is described. The potential of the reaction of hexafluoroacetone-protected phenylalanine with other aldehydes was scrutinized.

Original language	English
Pages (from-to)	1513-1518
Number of pages	6
Journal	Synthesis
Issue number	10
DOIs	https://doi.org/10.1055/s-2001-16091
State	Published - 2001
Externally published	Yes

Keywords

Amino acids
Cyclizations
Diastereoselectivity
Heterocycles
Quinolines

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10.1055/s-2001-16091

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title = "Asymmetric pictet-spengler reactions: Synthesis of 1,2,3,4-tetrahydroisoquinoline carboxylic acid (Tic) chimeras",

abstract = "A preparatively simple diastereoselective synthesis of the amino acid chimera (1S,3S)-1,2,3,4-tetrahydroisoquinoline-1,3-dicarboxylic acid from hexafluoroacetone-protected phenylalanine and glyoxylic acid hydrate via Pictet-Spengler reaction is described. The potential of the reaction of hexafluoroacetone-protected phenylalanine with other aldehydes was scrutinized.",

keywords = "Amino acids, Cyclizations, Diastereoselectivity, Heterocycles, Quinolines",

author = "J. Spengler and H. Schedel and J. Sieler and Quaedflieg, \{P. J.L.M.\} and Broxterman, \{Q. B.\} and Duchateau, \{A. L.L.\} and K. Burger",

year = "2001",

doi = "10.1055/s-2001-16091",

language = "Ingl{\'e}s",

pages = "1513--1518",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "10",

}

TY - JOUR

T1 - Asymmetric pictet-spengler reactions

T2 - Synthesis of 1,2,3,4-tetrahydroisoquinoline carboxylic acid (Tic) chimeras

AU - Spengler, J.

AU - Schedel, H.

AU - Sieler, J.

AU - Quaedflieg, P. J.L.M.

AU - Broxterman, Q. B.

AU - Duchateau, A. L.L.

AU - Burger, K.

PY - 2001

Y1 - 2001

N2 - A preparatively simple diastereoselective synthesis of the amino acid chimera (1S,3S)-1,2,3,4-tetrahydroisoquinoline-1,3-dicarboxylic acid from hexafluoroacetone-protected phenylalanine and glyoxylic acid hydrate via Pictet-Spengler reaction is described. The potential of the reaction of hexafluoroacetone-protected phenylalanine with other aldehydes was scrutinized.

AB - A preparatively simple diastereoselective synthesis of the amino acid chimera (1S,3S)-1,2,3,4-tetrahydroisoquinoline-1,3-dicarboxylic acid from hexafluoroacetone-protected phenylalanine and glyoxylic acid hydrate via Pictet-Spengler reaction is described. The potential of the reaction of hexafluoroacetone-protected phenylalanine with other aldehydes was scrutinized.

KW - Amino acids

KW - Cyclizations

KW - Diastereoselectivity

KW - Heterocycles

KW - Quinolines

UR - https://www.scopus.com/pages/publications/0034927038

U2 - 10.1055/s-2001-16091

DO - 10.1055/s-2001-16091

M3 - Artículo

AN - SCOPUS:0034927038

SN - 0039-7881

SP - 1513

EP - 1518

JO - Synthesis

JF - Synthesis

IS - 10

ER -

Asymmetric pictet-spengler reactions: Synthesis of 1,2,3,4-tetrahydroisoquinoline carboxylic acid (Tic) chimeras

Abstract

Keywords

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