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Asymmetric Synthesis of 3‐Hydroxyprolines by Photocyclization of N ‐(2‐Benzoylethyl)glycinamides
Author(s) -
Wessig Pablo,
Wettstein Philipp,
Giese Bernd,
Neuburger Markus,
Zehnder Margaretha
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770322
Subject(s) - chemistry , pyrrolidine , stereochemistry , medicinal chemistry
The chiral N ‐(2‐benzoylethyl)‐ N ‐tosylglycinamides 1a‐c were prepared from the C 2 ‐symmetric pyrrolidines 5a‐c . Irradiation of these ketones 1a‐c gave cis ‐3‐hydroxyprolinamides 10‐12 in moderate to good yields ( Scheme 3 ). The de of the photocyclizations depended on the size of the substituents in positions C(2) and C(5) of the chiral pyrrolidine auxiliaries. In addition, the de varied with the reaction temperature, allowing the determination of activation‐parameter differences. The structure of products 10‐12 were established by NMR and X‐ray analyses.

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