Beilstein J. Org. Chem.2007,3, No. 25, doi:10.1186/1860-5397-3-25
] were tested as well (Table 1, Entries 8–10), but they exhibited a significantly lower efficiency than the previous chlorinating agents.
Since N-chlorosuccinimide (NCS) had been applied for the oxidation of 4-(methylthio)morpholine towards the synthesis of diazasulfonium salts[22] and the preparation of
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Graphical Abstract
Scheme 1:
General synthesis of sulfonimidamides 3 from sulfinamides 1.
Beilstein J. Org. Chem.2005,1, No. 13, doi:10.1186/1860-5397-1-13
phenylglycine as previously described.[20]
In the first instance a Yb(OTf)3 mediated aza-Claisen rearrangement using allyl morpholine 10 and acid chloride 9 was explored following MacMillan's protocol.[21] This proceeded smoothly to give the α-fluoroamide 11 in good yield although reduction of the equivalence