Gold-catalysed synthesis of phosphonate-substituted oxetan-3-ones – an easy access to highly strained HWE reagents
Literature Information
Publication Date
2021-11-12
DOI
10.1039/D1QO01214B
Impact Factor
5.281
Authors
Shaista Tahir, Jonas F. Wunsch, Matthias Rudolph, Frank Rominger
View Original
Abstract
A convenient approach for the attainment of strained phosphonate-substituted oxetan-3-ones, starting from easy to synthesise alkynyl phosphonates, is presented. With the aid of a pyridine-N-oxide, in a gold-catalysed step an α-oxo carbene species is generated as a key intermediate. After formal OH-insertion, synthetically useful HWE reagents can be attained. The synthetic utility of the obtained building blocks could be demonstrated, which yielded the 2-alkenyl oxetan-3-one scaffold in high yields after the HWE reaction.
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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
![N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-beta-phenyl-L-phenylalanine structure](https://static.chemtradehub.com/structs/201/201484-50-6-c2fc.webp "N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-beta-phenyl-L-phenylalanine structure")
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-beta-phenyl-L-phenylalanine
CAS Number:
201484-50-6
Molecular Formula:
C30H25NO4
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