Oxygen nucleophiles alkenes alkynes allenes

Abstract Progress in the field of metal-catalyzed redox-neutral additions of oxygen nucleophiles (water, alcohols, carboxylic acids, and others) to alkenes, alkynes, and allenes between 2001 and 2009 is critically reviewed. Major advances in reaction chemistry include development of chiral Lewis acid catalyzed asymmetric oxa-Michael additions and Lewis-acid catalyzed hydro-alkoxylations of nonacti-vated olefins, as well as further development of Markovnikov-selective cationic gold complex-catalyzed additions of alcohols or water to alkynes and allenes. 

Progress in catalytic additions of oxygen nucleophiles to alkenes (Sect. 3), alkynes (Sect. 4), and allenes (Sect. 5) will now be discussed. 

Various oxygen nucleophiles such as water, alcohols, carboxylic acids, ketones, aldehydes, carbonates, amides, have been employed in gold catalysis to functionalize alkynes, allenes, or even alkenes [8], Their use allows the easy and generally efficient creation of at least one new C-O bond. A short selection of representative examples is shown in Scheme 16.13 [17]. 

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