C2-BIPNOR: An Easily Accessible Homologue of BIPNOR for Asymmetric Catalysis
journal contributionposted on 08.05.2006 by Magali Siutkowski, François Mercier, Louis Ricard, François Mathey
Any type of content formally published in an academic journal, usually following a peer-review process.
Under mild conditions at −78 °C, the McMurry coupling of the (R)-2-formyl-1-phosphanorbornadiene 2 yields the enantiopure (RP, SC, SC, RP) diol 4, dubbed C2-BIPNOR. In boiling THF, the same reaction leads to the trans-alkene 6. C2-BIPNOR is easier to prepare and to handle than BIPNOR while benefiting from the same configurational stability at phosphorus. It appears to have a wider range of catalytic applications than BIPNOR and, in one case (asymmetric Heck reaction), to be competitive with the best ligands proposed in the literature.