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20.2.1.6.4.2 Variation 2: With One- or Two-Carbon Homologation

DOI: 10.1055/sos-SD-020-00172

Evano, G.Science of Synthesis, (200720228.

Supplementary procedures rely on the use of organoboranes obtained by hydroboration of alkenes for CC bond formation, which is a well-documented process. Most of these reactions involve the formation of tetracoordinated organoborates 56 between the electron-deficient boron and a nucleophilic carbon atom. The complex formation is followed by the 1,2-intramolecular migration of an alkyl group from the boron atom to the adjacent carbon atom to give 57; these anionic rearrangements usually occur with substitution of a leaving group (Scheme 20).[‌130‌,‌131‌] With a proper choice of both the nucleophile and the organoborane involved in the process, this method can be useful for the synthesis of carboxylic acids from alkenes with one- or two-carbon homologation and even in an asymmetric way.

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References


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