Double‐Addition Reaction of Aryl Methyl Sulfones with N‐tert‐Butylsulfinyl Imines: Diastereoselective and Concise Synthesis of 2‐Sulfonylated 1,3‐Diamines

Abstract

We report a double-addition reaction of methyl phenyl sulfone and methyl 2-pyridyl sulfone with N-tert-butylsulfinyl imines. This method provides concise access to 2-sulfonylated 1,3-anti diamines with good to excellent diastereoselectivities. This protocol has the benefit of using readily accessible starting materials and is operationally simple.

Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

“…The same reaction shown in Scheme 26 was applied to imines 16 , so a double addition took place giving the corresponding sulfonylated diamines 67 (Scheme 27). [46] Desulfonylation of compounds 67 under radical conditions (Bu n 3 SnH/AIBN) gave sulfonylated diamines with C 2 symmetry (R=Ph, 4‐MeC 6 H 4 ; 60–63 %).…”

Construction of Chiral 1,3-Diamines through Rhodium-Catalyzed Asymmetric Arylation of Cyclic N-Sulfonyl Imines

“…Accordingly, various synthetic methods to access molecules containing a chiral 1,3-diamine framework have been developed. Asymmetric Mannich-type reaction using a certain type of nucleophiles such as nitriles or enamides can lead to 1,3-dinitrogen-containing products, but the generation of 1,3-diamines often requires further reduction with hydride reagents . The stereoselective ring-opening reaction of the substituted aziridines with nucleophiles could also provide highly enantioenriched 1,3-diamines efficiently .…”