Chiral Ligands with an Isoborneol-10-sulfonamide Structure: A Ten-Year Odyssey

Diego J. Ramón; Miguel Yus

doi:10.1055/s-2007-985602

ACCOUNT

Chiral Ligands with an Isoborneol-10-sulfonamide Structure: A Ten-Year Odyssey

Diego J. Ramón*, Miguel Yus*
Instituto de Síntesis Orgánica (ISO) and Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
Fax: +35(965)903549; e-Mail: djramon@ua.es; e-Mail: yus@ua.es;

Abstract

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Abstract

The isoborneol-10-sulfonamide unit represents a new type of chiral structure that has been successfully prepared and used in different reactions of organometallic addition to aldehydes and ketones. The obtained results were excellent in some cases, and this type of ligand is unique as it is able to promote the enantioselective addition of dialkylzinc reagents to simple ketones. The scope of these catalyzed reactions, together with some synthetic applications, is outlined. References to important related work from others are also included.

1 Introduction

2 First-Generation Ligands

2.1 Enantioselective Addition of Organozinc Reagents to Aldehydes

2.2 Enantioselective Addition to Ketones

3 Second-Generation Ligands

3.1 Enantioselective Addition of Organozinc Reagents to Aldehydes

3.2 Enantioselective Addition to Ketones

4 Third-Generation Ligands

5 Outlook

Key words

addition reactions - aldehydes - asymmetric catalysis - ketones - ligands

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