Preparation of (S)‐Nonafluorobutanesulfinamide

Abstract

The article reports preparation of (S)‐Nonafluorobutanesulfinamide. For the preparation of the perfluorobutanesulfinamide, we focused on Senanayake's chiral sulfinyl transfer auxiliary approach. The two‐step synthesis of perfluorobutanesulfinamide from Senanayakes's 2‐aminoindanol‐derived sulfinyl transfer reagent described in this report proceeds in good overall yield and with excellent enantiomeric purity. The described method uses inexpensive nonafluoro‐1‐iodobutane as a starting input and requires only one straightforward flash column chromatography. Additionally, the chiral auxiliary 3 can be recovered in good yields.

Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds

“…Later, Ellman and co-workers developed an improved synthesis of more electrophilic perfluorobutanesulfinamide 54 accomplished with the use of Senanayake’s 2-aminoindanol-derived sulfinyl transfer reagent 213 and a suitable Grignard reagent prepared from EtMgBr and C 4 F 9 I. 247 , 248 The sulfinate intermediate was treated with amine nucleophiles; NaHMDS led to the highest yield. The sulfinamide could be prepared on a gram scale in 67% yield and 99% ee using this two-step sequence ( Scheme 31 ).…”