کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5220901 1383403 2010 9 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
N-Carbamate α-aminoalkyl-p-tolylsulfones—convenient substrates in the nitro-Mannich synthesis of secondary N-carbamate protected syn-2-amino-1-nitroalkanephosphonates
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
N-Carbamate α-aminoalkyl-p-tolylsulfones—convenient substrates in the nitro-Mannich synthesis of secondary N-carbamate protected syn-2-amino-1-nitroalkanephosphonates
چکیده انگلیسی

An efficient one-pot synthesis of secondary N-carbamate protected syn-β-amino-α-nitroalkanephosphonates using diethyl nitromethanephosphonate and N-Boc or N-Cbz imines, generated in situ from stable N-Boc or N-Cbz α-aminoalkyl-p-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 N-carbamate protected syn-1,2-diaminoalkanephosphonates has also been elaborated.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 66, Issue 52, 24 December 2010, Pages 9840–9848