NOBIN

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NOBIN (2-amino-2'-hydroxy-1,1'-binaphthyl) is an organic molecule used for asymmetric catalysis. NOBIN is related to BINOL and other analogues by both having a chiral axis and being a scaffold for certain chemical reactions. NOBIN is an excellent catalyst for the Aldol reaction producing reliable products, good yield and excellent diastereoselectivity

Rotation around the adjoining bond of the 2 adjacent rings is limited by the hydrogens limiting tautomerisation. enantiomerically pure nobin may racemise with heat.

NOBIN is prepared by oxidative cross coupling of 2-naphthol and 2-naphthylamine. The oxidative source is metal ions in solution such as Fe²⁺ or a Cu²⁺ amine complex. Once racemic NOBIN is produced it needs to be resolved. One method for this is the use of camphorsulfonic acid, in which the basic group of NOBIN is used to form a diastereomeric salt of one enantiomer. The other enantiomer however will stay in solution.

[edit] References

• Kocovsky, Smrcina, Lorenc, Hanus; Synlett;(1991) 231
• Ding, Li; Ten years of research on NOBIN chemistry: Current Organic Synthesis;(2005);2;499-545