Ein neuer Zugang zu enantiomerenreinen β‐Lactamen aus α‐Aminosäuren durch präparative Anwendung der Isonitril‐Nitril‐Umlagerung | Zendy

Haaf Klaus | Zendy; Rüchardt Christoph | Zendy

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Ein neuer Zugang zu enantiomerenreinen β‐Lactamen aus α‐Aminosäuren durch präparative Anwendung der Isonitril‐Nitril‐Umlagerung

Author(s) -

Haaf Klaus,

Rüchardt Christoph

Publication year - 1990

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19901230333

Subject(s) - chemistry , nitrile , stereospecificity , stereochemistry , organic chemistry , catalysis

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.

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