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2.9.2.3.3 Rhodium-Catalyzed Addition of Alkenyltrifluoroborates

DOI: 10.1055/sos-SD-202-00221

Kauffman, M. C.; Walsh, P. J.Science of Synthesis: Stereoselective Synthesis, (20112490.

In the rhodium-catalyzed additions of alkenyltrifluoroborates, both aromatic and aliphatic imines can be used to form the N-(hex-2-enyl)sulfinamides 70 (Scheme 35). The stereochemical outcome of these reactions is determined by the use of chiral N-(tert-butylsulfinyl)imines.[‌172‌] The addition takes place with high yield and diastereomeric ratio using both electron-poor and electron-neutral arylimines. Sensitive functional groups on the aryl group and sterically hindered aryl groups are also tolerated. The use of electron-rich aryl groups results in a reduction in the yield. A variety of alkenyl groups can be used; however, electron-poor alkenyltrifluoroborates give lower yields. Unbranched and δ-branched aliphatic imines undergo alkenyl addition in a good yield and high diastereoselectivity, whereas the use of α- and β-branched imines result in lower yields. Representatives of all these reaction types are depicted in Scheme 35.[‌172‌]

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