Catalytic kinetic resolution and directed hydrogenation

Since the sense of diastereoselective hydrogen addition is common to almost all the examples tested, it should conform to a predictive model which can be set in the general context of addition reactions of acyclic olefins with an a-chiral centre. Much effort has been expended to explaining such addition reactions with electrophilic reagents, which follow a predictable pattern in several cases. The relevant factors are the energies of the possible gound-state 

Hydroboration 9-BBN Peracid epoxidation Simmons-Smith cyclopropanation Cyclopropanation with CH2I2 / Sm(Hg) Cyclopropanation with CCI2 lodoacetoxylation 

Catalytic hydroboration (catecholborane/Rh) Catalytic osmylation Titanium-promoted epoxidation Catalytic hydrosilylation with (Me2H)Sl2NH Rh or Ru-directed hydrogenation 

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