N-Sulfinyl imine

The N-sulfinyl group exerts powerful and predictable stereodirecting effects resulting in high levels of asymmetric induction.

The addition of organometallic reagents to N-sulfinyl imines is the most reliable and versatile method for the asymmetric synthesis of amine derivatives.

[13] More practical is the one-pot procedure from the Andersen reagent making a variety of p-toluene-sulfinyl imines available from both aromatic and aliphatic aldehydes.

[14] A widely used method for the asymmetric synthesis of N-sulfinyl imines is the condensation of enantiopure primary sulfinamides with aldehyde or ketones.

[8] Mild acid treatment readily removes the N-sulfinyl group in the sulfinamide products affording the free amine derivatives.

Sulfinimine
Structure of 4-ClC 6 H 4 CH=NS(O)Bu- t . Selected distances: d S=O = 147.5, d N=C = 127.5, d S-N = 170.4 pm. [ 17 ] Color scheme: red = O, blue = N, green = Cl, gray = C, white = H, yellow = S.