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Where other common chiral ligands failed, (−)-sparteine can be employed to form complexes with Grignard reagents. These chirally modified reagents desymmetrize a range of anhydrides with good enantioselectivity (up to 92 % ee; see scheme). Whereas (−)-sparteine is well known to form complexes with organolithium reagents and to induce excellent enantioselection in their reactions with electrophiles, (−)-sparteine-controlled asymmetric processes that involve Grignard reagents are rare.
Shintani et al. (Fri,) studied this question.