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Secondary amines do it too! Catalytic asymmetric insertion of α-diazoesters in the NH bond of differently substituted amines has been successfully achieved (see scheme; M.S.=molecular sieves). For a wide substrate scope, excellent enantioselectivities (up to 98 % ee) and high yields (up to 99 %) were obtained under mild reaction conditions.
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Hou et al. (2010) studied this question.
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