The first solid-phase synthesis of bis(oxazolinyl)pyridine ligands

Avi Weissberg; Baruch Halak; Moshe Portnoy

doi:10.1021/jo050237j

The first solid-phase synthesis of bis(oxazolinyl)pyridine ligands

Avi Weissberg, Baruch Halak, Moshe Portnoy^*

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

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

52 Scopus citations

Abstract

Chiral Pybox (pyridine-2,6-bis(oxazoline)) ligands can be cleanly and efficiently prepared on polystyrene support via a five-step solid-phase synthetic sequence. Cu(I)-complexed polymer-bound Pybox was used as a catalyst in the first heterogeneously catalyzed asymmetric addition of alkynes to imines. Best enantioselectivity was observed with ^tBu-substituted oxazolines.

Original language	English
Pages (from-to)	4556-4559
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	11
DOIs	https://doi.org/10.1021/jo050237j
State	Published - 27 May 2005

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abstract = "Chiral Pybox (pyridine-2,6-bis(oxazoline)) ligands can be cleanly and efficiently prepared on polystyrene support via a five-step solid-phase synthetic sequence. Cu(I)-complexed polymer-bound Pybox was used as a catalyst in the first heterogeneously catalyzed asymmetric addition of alkynes to imines. Best enantioselectivity was observed with tBu-substituted oxazolines.",

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AB - Chiral Pybox (pyridine-2,6-bis(oxazoline)) ligands can be cleanly and efficiently prepared on polystyrene support via a five-step solid-phase synthetic sequence. Cu(I)-complexed polymer-bound Pybox was used as a catalyst in the first heterogeneously catalyzed asymmetric addition of alkynes to imines. Best enantioselectivity was observed with tBu-substituted oxazolines.

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The first solid-phase synthesis of bis(oxazolinyl)pyridine ligands

Abstract

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