Enantioselective cyclopropanation of allylic alcohols using chiral catalysts

Enantioselective cyclopropanation of allylic alcohols using chiral catalysts 

Cyclopropanation of olefins (Simmons-Smith reaction) smoothly proceeds using diethylzinc in combination with diiodomethane. The reaction is much faster with allylic alcohols or its ether derivatives than that with simple olefins. 

There is only one example of a catalytic enantioselective cyclopropanation of allylic alcohols using an electron withdrawing chiral disulfonamide 19 as a chiral ligand (Protocol 6).33 Stoichiometric highly enantioselective cyclo-propanations of allylic alcohols are reported using a chiral diethyl tartrate34 and a chiral tartamide.35 

Enantioselective cyclopropanation of an allylic alcohol using chiral disulfonamide (Structure 19) as a chiral catalyst336 

Caution Carry out all procedures in a well-ventilated hood, and wear disposable vinyl and/or latex gloves and chemical-resistant goggles at all times. 

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