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A highly efficient nickel-catalyzed asymmetric alkylative coupling of alkynes, aldehydes, and dimethylzinc has been realized by using bulky spirobiindane phosphoramidite ligands, affording allylic alcohols with a tetrasubstituted olefin functionality in high yields, high regioselectivities, and excellent enantioselectivities.

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The nickel-catalyzed reductive coupling of alkynes and imines with Et(2)Zn as a reductant by using electron-rich phosphine ligands has been developed, affording various allylic amines with high yields and excellent chemoselectivities. Chiral induction was also achieved in this reductive coupling reaction when a nickel catalyst containing a chiral spiro phosphine ligand was used.

A catalytic asymmetric version of the intramolecular ylide annulation has been developed which affords high ee values and diastereoselectivities and which further shows that spirobiindanebased chiral phosphines can be excellent organocatalysts. Both optically active benzobicycloA C H T U N G T R E N N U N G [4.3.0] compounds 2 and 2' with three continuous stereogenic centers could be obtained as major products selectively under neutral and mild conditions just by a choice of an additive.