In:
Angewandte Chemie, Wiley, Vol. 128, No. 46 ( 2016-11-07), p. 14469-14473
Abstract:
The first example of organocatalyzed γ′‐selective functionalization of cyclic enones with 3‐substituted maleimides results in the stereoselective construction quaternary carbon center is presented. The reactions provided γ′‐functionalized cyclic enones and β‐functionalized cyclopentenones in good to excellent yields with excellent diastereo‐ and enantioselectivities. DFT calculations indicated that the reaction might proceed as a [4+2] cycloaddition/retro‐Mannich reaction which could explain the unexpected product with a chiral quaternary carbon center and the excellent stereoselectivity.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v128.46
DOI:
10.1002/ange.201605790
Language:
English
Publisher:
Wiley
Publication Date:
2016
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