N-Carbamate α-aminoalkyl-p-tolylsulfones - Convenient substrates in the nitro-Mannich synthesis of secondary N-carbamate protected syn-2-amino-1-nitroalkanephosphonates
摘要：
An efficient one-pot synthesis of secondary -carbamate protected -β-amino-α-nitroalkanephosphonates using diethyl nitromethanephosphonate and -Boc or -Cbz imines, generated in situ from stable -Boc or -Cbz α-aminoalkyl--tolylsulfones has been developed under PTC conditions. A model enantioselective version of this reaction is also described. Enantioselectivity up to 67% ee is achieved using a chiral thiourea catalyst derived from a cinchona alkaloid. Completely stereoselective conversion of the title compounds into partially -carbamate protected -1,2-diaminoalkanephosphonates has also been elaborated.Graphical abstract
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关键词：
Diethyl nitromethanephosphonate α-Amido sulfones PTC reaction Aminonitrophosphonates 2-Diaminoalkanephosphonates
DOI：
10.1016/j.tet.2010.10.072
被引量：
年份：
2010
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