Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes
摘要:
The first enantioselective Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes has been realized by using a new bifunctional Takemoto-type thiourea catalyst. The primary Michael adducts obtained were converted in situ to the corresponding amides through the aminolysis. High yields, excellent diastereoselectivities (>95:5 dr), and good enantioselectivities (up to 81% ee) have been achieved for the corresponding α,β-disubstituted γ-nitroamides. This reaction again demonstrated that α-ketophosphonates are interesting pronucleophiles that can be used as amide surrogates in organocatalyzed reactions.
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关键词:
Michael reaction Organocatalysis α-Ketophosphonate Nitroalkene Enantioselective Amide surrogate
DOI:
10.1016/j.tetlet.2013.08.015
被引量:
年份:
2013
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