Tk. Yang et al., APPLICATION OF NEW CAMPHOR-DERIVED MERCAPTO CHIRAL AUXILIARIES TO THESYNTHESIS OF OPTICALLY-ACTIVE PRIMARY AMINES, Journal of organic chemistry, 59(4), 1994, pp. 914-921
A series of enantiomerically pure sulfinimines carrying new camphor-ba
sed mercapto chiral auxiliaries are subjected to asymmetric alkylation
. Such reaction offers an excellent route to the preparation of optica
lly active primary amines. Also reported here is an unprecedented Grig
nard addition of a chiral sulfenimine leading to a single enantiomer o
f the corresponding sulfenamide and thence produced enantiopure amine
after acidic aqueous workup. The chiral auxiliary can be recovered in
high yield.