ISSN:
0009-2940
Keywords:
β-Lactams / Isonitrile-nitrile rearrangement / α-Amino acids
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A New Approach to Enantiomerically Pure β-Lactams from a-Amino Acids by Applying the Isonitrile-Nitrile Rearrangement(S)-Phenylalanine (1) was converted into (S)-3-benzyl-2-azetidinone (8b) by a multistep reaction sequence. The key step of this approach is a stereospecific isonitrile-nitrile rearrangement (3 → 4) by flash pyrolysis, which may be performed in 20-g batches of 3. An improved procedure for the preparation of (S)-Phenylalaninol (2a) is described.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230333