Norbomene hydroboration

Asymmetric Hydroboration. Hydroborations of alkenes by catecholborane have been catalyzed by [Rh(Cl)(cod)-(diphosphine)]. For example, norbomene gives, after oxidation, exo-norbomeol (82% ee) when a DIOP derivative (2-MeO-DIOP) was used (eq 5). Lower ee s were observed with DIOP, DIPAMP, and BINAP. The effectiveness of DIOP was also noticed in another report. ... 

Protonolysis occurs with retention of stereochemistry at the carbon atom originally attached to boron.Thus, by use of a deuteriated hydroborating agent e.g. 9-BBN-D) or of a deuteriated carboxylic acid, or both, deuterium atoms can be introduced at specific and predictable locations in a molecule. An example is the conversion of 2-norbomene into ej o,ej o-2,3-dideuterionorbomane (equation 56). ... 

RCH=CHi — RCH CH Hi. Brown and co-workers " found that an alkylborane resulting from hydroboration of an olefin reacts readily with either chloramine or hydroxylamine-O-sulfonic acid to form the corresponding amine in yield of 50-60%. For example, norbomene yields exo-norbornylamine. 

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