Reactions of Amines. XI. Synthesis of α-Amino Ketones from Ketimines<sup>1,2</sup>

Baumgarten, Henry E.; Petersen, James M.; Wolf, Donald C.

doi:10.1021/jo01044a052

Search citation statements

Order By: Relevance

Paper Sections

Select...

E Limitations Of the Reaction1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1964

2010

Publication Types

Select...

Article3

Other3

Relationship

Self Cite0

Independent6

Authors

Journals

Cited by 13 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Accordingly, they suggested that the reaction was limited to structures which did not contain a methinyl group adjacent to the oxime function. In the related rearrangements of N-chloroketimines and dimethylhydrazone methiodides to -amino ketones (section IIIB), no such structural limitation exists, and the rearrangement of isopropyl phenyl N-chloroketimine afforded «-aminoisobutyrophenone hydrochloride in 20-35% yield (6) while the rearrangement of isobutyrophenone dimethylhydrazone methiodide gave the same amino ketone in 75% yield (32).…”

Section: E Limitations Of the Reactionmentioning

confidence: 99%

The Rearrangement of Ketoxime O-Sulfonates to Amino Ketones (The Neber Rearrangement)

O’Brien¹

1964

Chem. Rev.

119

View full text Add to dashboard Cite

Section: E Limitations Of the Reactionmentioning

confidence: 99%

The Rearrangement of Ketoxime O-Sulfonates to Amino Ketones (The Neber Rearrangement)

O’Brien¹

1964

Chem. Rev.

119

View full text Add to dashboard Cite

Baumgarten α‐Amino Ketone Synthesis

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

The synthesis of α‐amino ketones from the rearrangement of N , N ‐dichloro‐ sec ‐alkylamines by means of the treatment of sodium methoxide and this reaction is referred as Baumgarten α‐amino ketone synthesis. It is a specific method to synthesize α‐amino ketones and α‐amino acids. This reaction has also been modified for preparing α‐amino ketones from the reaction between more generally available nitriles and a Gringard reagent.

show abstract