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Please login to access the full content or check if you have access via2.9.2.3.3 Rhodium-Catalyzed Addition of Alkenyltrifluoroborates
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Kauffman, M. C.; Walsh, P. J., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 490.
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]
Meeeee 88 Meeeeee-Meeeeeeee Meeeeeeeeeee ee Meeeeeeee eee Meeeeeee Meeeee[888]
M8 | ee | Meeee (%) | Mee |
---|---|---|---|
Me | 88:8 | 88 | [888] |
8-Mee | >88:8 | 88 | [888] |
8-MeM8M8 | 88:8 | 88 | [888] |
8-MeMM8M8 | 88:8 | 88 | [888] |
(MM8)8Me | 88:8 | 88 | [888] |
(MM8)8eMe | 88:8 | 88 | [888] |
MM8Me | 88:8 | 88 | [888] |
Me | 88:8 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
M-(Mee-8-eeee)eeeeeeeeeeee 88; Meeeeee Meeeeeeee:[888]
Meeeeeee MMM (8.88 M ee 8.88 M) eee eeeee ee eeeeeee ee eeeeeeeee-8,8-eeeee(eeeeeee)eeeeeee(M) eeeee (8.88–8.888 eeeee) eee 8,8-eee(eeeeeeeeeeeeeeeee)eeeeeee (8.88–8.888 eeeee). Mee eeeeeeeee eeee eee eeeee ee eeeeeee ee eee eeeeeeeee eeeeeeeeeeeeeeeeeeeeee (8.8 eeeee) eee eee eeeeeee eee eeeee ee eeeeeee ee eee eeeeeeee eeeeeeeeeeeee (8.8 eeeee). Meeeeeee M8M (8.88 M ee 8.88 M) eee eeee eeeeeeeeee ee eeeeeee eee eeeeeeee Me8M (8.8 eeeee) eee eeeee ee eeeeeeee eeeeeee. Mee eeeeeee eee eeeeeee eee 88 e ee 88 °M, eeee, eeeee eeeeeee ee ee, ee eee eeeeeee eeee MeMMe/eeeeeee (8:8). Mee eeeeeee eeeee eee eeeeee eeee M8M, eee eee eeeeeee eeeee eee eeeeeeeee eeee MeMMe/eeeeeee (8:8; 8 ×). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeee eeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee).
References
[172] | Meee, M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |