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Wang, K. K., Science of Synthesis, (2008) 44, 229.
General Introduction
Synthesis of allenes by addition reactions encompasses the 1,4-addition of substrates to conjugated enyne systems. A variety of substrates, such as lithium aluminum hydride, hydroboranes, hydrosilanes, hydrogen halides, halogens, organometallic reagents, carbon pronucleophiles, and acyl chlorides are used. Conjugate additions of organometallic reagents to ynoates, ynones, and acceptor-substituted enynes also represent major synthetic tools for the preparation of allenes. Condensation between propargylic organometallic reagents and carbonyl and related compounds is especially efficient for the preparation of α-allenic alcohols and related adducts. The success of many of these addition reactions depends on high regioselectivity at the initial point of attack and the ability to capture the resulting adduct with an electrophile regioselectively. The possibility to connect two or three separate fragments together in a single operation provides efficient pathways for allenes with diverse structural features. These addition reactions are also inherently efficient in terms of atom economy.
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