Chiral allylic amines hydroboration

Hydroboration of Chiral Allyl Amines and Chiral Allyl Alcohols... 

Ferrocenyl-based ligands comprise a versatile class of auxiliaries because they can be easily modified at the benzylic position with retention of configuration and can incorporate both central and planar chiralities. The appropriate balance of steric and electronic factors has provided ferrocenyl derivatives featuring chelating P,N properties that proved beneficial in numerous enantioselective transformations [50]. Among more recent applications, they could be utilized very efficiently in Pd-catalyzed hydrosilylation (14 >99% ee) [51] and hydroboration (>94% ee) [52] of olefins, allylic amination (99 % ee) [53], Suzuki cross coupling reactions (Section 2.11) [54], and enamide hydrogenation (>99% ee) [55]. 

Substrate-controlled diastereoselective hydroboration of protected chiral allylic alcohols [25-27] or amines [28, 29] with 9-BBN gives almost always anti selective products. On the other hand, catalyzed hydroboration in most of the cases using catecholborane as hydroborating agent tends to be syn selective [28-30] (Eq. 5.9). 

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