Synlett 2008(19): 3075-3076  
DOI: 10.1055/s-2008-1067280
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Nitrosobenzene

Fernanda Lacerda Silva da Machado*
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, 21941-590 Rio de Janeiro, Brazil
e-Mail: flacerdas@yahoo.com.br;
Further Information

Publication History

Publication Date:
12 November 2008 (online)

Introduction

Nitrosobenzene is a reagent used in many asymmetric syntheses with amazing results. It acts as an electrophile in catalytic enantioselective carbon-nitrogen and carbon-oxygen bond-forming reactions. It has received attention in recent years because of its high reactivity and regio- and stereoselectivities. In the presence of Lewis or ­Brønsted acid catalysts, enantioselective nitroso aldol or ­nitroso Diels-Alder reactions proceed under smooth conditions. [¹] Nitrosobenzene can be used in the aminoxylation of aldehydes and ketones, and the products are precursors of 1,2-amino alcohols, terminal diols [²] and allylic alcohols. [³] It can also be used in asymmetric desymmetrization of α-hydroxy ketones. [4] Others applications are described below. This reagent is stable, inexpensive and commercially available, all of which corroborate its use.

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