Efficient synthesis of (Z)- and (E)-methyl 2-(methoxyimino)-2-phenylacetate

Authors :: Wu, Yong-Jin
Huang, Stella
Ng, Alicia
Gao, Qi
Roy Kimura, S.
Langley, David R.
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Apr2010, Vol. 51 Issue 16, p2144-2147. 4p.
Publication Year :: 2010
Abstract: Abstract: Direct oximation of 2-oxo-2-phenylacetate (3) gave the (Z)-methyl 2-(methoxyimino)-2-phenylacetate (1) in 71% yield, while the E oxime 2 was prepared from 3 in 65% yield via oxime isomerization of 2-(methoxyimino)-2-phenylacetic acid (5). Computational studies suggest that the isomerization of 5 is thermodynamically driven, while the direct oximation of ketoester 3 is kinetically controlled. [Copyright &y& Elsevier]

Subjects :: *ORGANIC synthesis
*PHENYLACETATES
*OXIMES
*ISOMERIZATION
*PHENYLACETIC acid
*THERMODYNAMICS
*ESTERS
*CHEMICAL kinetics

Language :: English
ISSN :: 00404039
Volume :: 51
Issue :: 16
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 48723569
Full Text :: https://doi.org/10.1016/j.tetlet.2010.02.073