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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.