Highly Enantioselective Catalytic Asymmetric [2+2] Cycloadditions of Cyclic [alpha]-Alkylidene [beta]-Oxo Imides with Ynamides

Highly Enantioselective Catalytic Asymmetric [2+2] Cycloadditions of Cyclic [alpha]-Alkylidene [beta]-Oxo Imides with Ynamides

Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic [alpha]-alkylidene [beta]-oxo imides with ynamides are described. The high reactivity of the cyclic [alpha]-alkylidene [beta]-oxo imide allows the [2+2] cycloadditions of a hindered substrate with unreactive ynamides at low...

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Veröffentlicht in:Chemistry : a European journal 2015-02, Vol.21 (7), p.2798
Hauptverfasser: Enomoto, Kazuaki, Oyama, Harufumi, Nakada, Masahisa
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Oyama, Harufumi
Nakada, Masahisa
description Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic [alpha]-alkylidene [beta]-oxo imides with ynamides are described. The high reactivity of the cyclic [alpha]-alkylidene [beta]-oxo imide allows the [2+2] cycloadditions of a hindered substrate with unreactive ynamides at low temperature. The X-ray crystallographic analysis of the product suggests that the enantioselectivity of the [2+2] cycloaddition can be well explained by the chelate model comprising the intramolecular hydrogen bond, wherein the cyclic [alpha]-alkylidene [beta]-oxo imide coordinates with CuII through the two imide carbonyls. The imide group in the product can be transformed to amide, nitrile, and ester groups; moreover, it is removable.
doi_str_mv 10.1002/chem.201406189
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title Highly Enantioselective Catalytic Asymmetric [2+2] Cycloadditions of Cyclic [alpha]-Alkylidene [beta]-Oxo Imides with Ynamides
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