Reagent-controlled regiodivergence in the [3,3]-sigmatropic rearrangement of N-(acyloxy)enamides
Literature Information
Publication Date
2019-09-27
DOI
10.1039/C9QO01109A
Impact Factor
5.281
Authors
Norihiko Takeda, Narumi Arisawa, Misaki Miyamoto, Yukiko Kobori, Tetsuro Shinada, Masafumi Ueda
View Original
Abstract
A regiodivergent [3,3]-sigmatropic rearrangement of N-(acyloxy)enamides has been developed. The regioselectivity of the rearrangement based on the N–O bond cleavage was complementarily controlled by changing reaction conditions. The treatment of enamides with LiHMDS afforded enamido carboxylic acid via C–C bond formation, while the reaction with 2,4,6-collidine under thermal conditions afforded an enamido ester via C–O bond formation.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
(S)-1-(3-(Benzyloxy)phenyl)-3-(dimethylamino)-2-methylpropan-1-one (2r,3r)-2,3-bis(benzoyloxy)succinate
CAS Number:
1004315-81-4
Molecular Formula:
C37H37NO10
2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl bromide
CAS Number:
4753-07-5
Molecular Formula:
C26H35BrO17
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