Diphenylmethyl imines

Homochiral 3,3 -dimethyl-2,2 -bisquinoline N,N -dioxide serves as a Lewis base catalyst for asymmetric hydrocyanation of aromatic N-(diphenylmethyl)imines, although the enantioselectivity is still modest (37-77% ee) [659]. 

Imines are particularly useful reagents when hindered electrophiles are considered. In this context, A-(oc-methylbenzylidene)benzylamines have been described as alternatives to acetophenones. " Similarly A-methylbenzophenonimine serves as an alternative to benzophenone ° itself in reactions with 2-phenyl-5(477)-oxazolone 146 to prepare 2-phenyl-4-(a-phenylethylidene)- and 4-(diphenylmethyl-ene)-2-phenyl-5(4//)-oxazolone, respectively. 

Sequential catalytic hydrogenation of the imine bond followed by hydrogenoly-sis of the resultant yV-diphenylmethylamine is an alternative method of deprotection which was used in a solid-phase synthesis of O-glycosyl cyclic Enkephalin analogues [Scheme 8.236]. Note the comprehensive deprotection of 4 benzyl ethers, a diphenylmethyl ester, and an N-diphenylmethyleneamine in a single operation. iV-Diphenylmethyleneamine derivatives of serine have also been applied to the synthesis of Sphingosines. ... 

---