Anion‐receptor molecules: Synthesis of a chiral and functionalized binding subunit, a bicyclic guanidinium group derived from L‐ or D‐ asparagine

Antonio Echavarren; Amalia Galán; Javier de Mendoza; Armando Salmerón; Jean‐Marie Lehn

doi:10.1002/hlca.19880710402

Anion‐receptor molecules: Synthesis of a chiral and functionalized binding subunit, a bicyclic guanidinium group derived from L‐ or D‐ asparagine

Antonio Echavarren
, Amalia Galán
, Javier de Mendoza^*
, Armando Salmerón
, Jean‐Marie Lehn

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

43 Citations (Scopus)

Abstract

The optically active (4S,8S)‐4, 8‐bis(hydroxymethyl)‐1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene ((S,S)‐1) has been synthesized in nine steps from L‐asparagine with a total yield of 5.1%. Similarly, the enantiomer (R,R)‐1 has been prepared from D‐asparagine. (S,S)‐ and (S,S)‐1 are representative examples of rigid and functionalized bicyclic guanidine systems and constitute useful intermediates in the construction of chiral selective anion‐receptor molecules. Copyright © 1988 Verlag GmbH & Co. KGaA, Weinheim

Original language	English
Pages (from-to)	685-693
Journal	Helvetica Chimica Acta
Volume	71
Issue number	4
DOIs	https://doi.org/10.1002/hlca.19880710402
Publication status	Published - 15 Jun 1988
Externally published	Yes

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Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

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title = "Anion‐receptor molecules: Synthesis of a chiral and functionalized binding subunit, a bicyclic guanidinium group derived from L‐ or D‐ asparagine",

abstract = "The optically active (4S,8S)‐4, 8‐bis(hydroxymethyl)‐1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene ((S,S)‐1) has been synthesized in nine steps from L‐asparagine with a total yield of 5.1\%. Similarly, the enantiomer (R,R)‐1 has been prepared from D‐asparagine. (S,S)‐ and (S,S)‐1 are representative examples of rigid and functionalized bicyclic guanidine systems and constitute useful intermediates in the construction of chiral selective anion‐receptor molecules. Copyright {\textcopyright} 1988 Verlag GmbH \& Co. KGaA, Weinheim",

author = "Antonio Echavarren and Amalia Gal{\'a}n and \{de Mendoza\}, Javier and Armando Salmer{\'o}n and Jean‐Marie Lehn",

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volume = "71",

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Anion‐receptor molecules: Synthesis of a chiral and functionalized binding subunit, a bicyclic guanidinium group derived from L‐ or D‐ asparagine. / Echavarren, Antonio; Galán, Amalia; de Mendoza, Javier et al.
In: Helvetica Chimica Acta, Vol. 71, No. 4, 15.06.1988, p. 685-693.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

TY - JOUR

T1 - Anion‐receptor molecules

T2 - Synthesis of a chiral and functionalized binding subunit, a bicyclic guanidinium group derived from L‐ or D‐ asparagine

AU - Echavarren, Antonio

AU - Galán, Amalia

AU - de Mendoza, Javier

AU - Salmerón, Armando

AU - Lehn, Jean‐Marie

N1 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

PY - 1988/6/15

Y1 - 1988/6/15

N2 - The optically active (4S,8S)‐4, 8‐bis(hydroxymethyl)‐1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene ((S,S)‐1) has been synthesized in nine steps from L‐asparagine with a total yield of 5.1%. Similarly, the enantiomer (R,R)‐1 has been prepared from D‐asparagine. (S,S)‐ and (S,S)‐1 are representative examples of rigid and functionalized bicyclic guanidine systems and constitute useful intermediates in the construction of chiral selective anion‐receptor molecules. Copyright © 1988 Verlag GmbH & Co. KGaA, Weinheim

AB - The optically active (4S,8S)‐4, 8‐bis(hydroxymethyl)‐1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene ((S,S)‐1) has been synthesized in nine steps from L‐asparagine with a total yield of 5.1%. Similarly, the enantiomer (R,R)‐1 has been prepared from D‐asparagine. (S,S)‐ and (S,S)‐1 are representative examples of rigid and functionalized bicyclic guanidine systems and constitute useful intermediates in the construction of chiral selective anion‐receptor molecules. Copyright © 1988 Verlag GmbH & Co. KGaA, Weinheim

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DO - 10.1002/hlca.19880710402

M3 - RGC 21 - Publication in refereed journal

SN - 0018-019X

VL - 71

SP - 685

EP - 693

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 4

ER -

Anion‐receptor molecules: Synthesis of a chiral and functionalized binding subunit, a bicyclic guanidinium group derived from L‐ or D‐ asparagine

Abstract

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