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Merrifield Resin Supported Copper Catalyst for Asymmetric Cyclopropanation

H. Werner, C. I. Herrerías, M. Glos, A. Gissibl, J. M. Fraile, I. Pérez, J. A. Mayoral, O. Reiser

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Abstract

Significance A recyclable Merrifield resin supported copper catalyst for asymmetric cyclopropanation of styrene was developed. Aza(bisoxazoline) ligand 1 was attached to the Merrifield resin and the resulting immobilized ligand 2 was evaluated in copper(I)-catalyzed asymmetric cyclopropanation. The cyclopropanation of styrene with ethyl diazoacetate by using Cu(OTf) 2 · 2 (1 mol%) gave the trans / cis isomers of the cyclopropanation products in a 74:26 ratio in 94% yield with 99% ee ( trans ) and 90% ee ( cis ), respectively. This supported catalyst was reused without loss of selectivity (see scheme).

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What this paper is about

Significance A recyclable Merrifield resin supported copper catalyst for asymmetric cyclopropanation of styrene was developed. Aza(bisoxazoline) ligand 1 was attached to the Merrifield resin and the resulting immobilized ligand 2 was evaluated in copper(I)-catalyzed asymmetric cyclopropanation. The cyclopropanation of styrene with ethyl diazoacetate by using Cu(OTf) 2 · 2 (1 mol%) gave the trans / cis isomers of the cyclopropanation products in a 74:26 ratio in 94% yield with 99% ee ( trans ) and 90% ee ( cis ), respectively. This supported catalyst was reused without loss of selectivity (see scheme).

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Available abstract

Significance A recyclable Merrifield resin supported copper catalyst for asymmetric cyclopropanation of styrene was developed. Aza(bisoxazoline) ligand 1 was attached to the Merrifield resin and the resulting immobilized ligand 2 was evaluated in copper(I)-catalyzed asymmetric cyclopropanation. The cyclopropanation of styrene with ethyl diazoacetate by using Cu(OTf) 2 · 2 (1 mol%) gave the trans / cis isomers of the cyclopropanation products in a 74:26 ratio in 94% yield with 99% ee ( trans ) and 90% ee ( cis ), respectively. This supported catalyst was reused without loss of selectivity (see scheme).

Key concepts: Cyclopropanation, Ethyl diazoacetate, Copper, Chemistry, Catalysis, Styrene, Ligand (biochemistry), Yield (engineering)

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