ISSN:
0947-3440
Keywords:
Asymmetric synthesis
;
Ring transformations
;
Lactons
;
Lactams
;
Pyrazolidin-3-one
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
α,β-Unsaturated lactones or lactams 1 react with hydrazines 2 via Michael-like addition and subsequent ring transformation by nucleophilic attack of the hitherto unchanged hydrazine nitrogen atom at the carbonyl carbon atom. The addition is highly trans-stereoselective, thus affording optically active hydroxylalkyl- or aminoalkylpyrazolidin-3-ones 4 and 6. These pyrazolidin-3-ones are further transformed to tosylated, acetylated or silylated derivatives 9 or react with benzaldehyde to give the azomethine imine 10.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961013
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