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7.6.11.2.3 Variation 3: Nickel-Catalyzed Enantioselective Coupling of Grignard Reagents with Allyl Compounds

DOI: 10.1055/sos-SD-007-00562

Takahashi, T.; Liu, Y.Science of Synthesis, (20047600.

There are several chiral phosphines ligands commonly used for the enantioselective ­coupling of Grignard reagents with allyl compounds: ()-Diop,[‌31‌] (S,S)-Chiraphos,[‌20‌,‌32‌‌36‌] (R)-Phenphos,[‌35‌] (+)-(R,R)-cyclopentane-1,2-diylbis(diphenylphosphine) (Scheme 6),[‌37‌] ­BIPHEMP, MeO-BIPHEP, (S)-BINAP, (S,R)-BPFFA, optically active oxazolinylferrocenylphosphine,[‌38‌] and 3,4-bis(diphenylphosphino)pyrrolidine.[‌39‌] Among these chiral phosphine ­ligands, (S,S)-Chiraphos is widely used for the coupling of allyl compounds, giving good results, and in some cases enantiomeric excesses of over 90% are obtained.

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