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Asymmetric Syntheses via Heterocyclic Intermediates, XLII. Asymmetric Syntheses of Diastereomerically and Enantiomerically Pure (2 R ,3 S )‐ threo ‐3‐Arylserine Methyl Esters by the Bislactim Ether Method Asymmetric Synthesis of Chloramphenicol
Author(s) -
Schöllkopf Ulrich,
Beulshausen Tessa
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890143
Subject(s) - chemistry , ether , yield (engineering) , hydrolysis , stereochemistry , derivative (finance) , dipeptide , organic chemistry , amino acid , biochemistry , materials science , economics , financial economics , metallurgy
The titanium derivative 3 of the bislactim ether 1 of cyclo(‐ L ‐Val‐Gly‐) reacts with arylaldehydes 4 highly diastereoselectively to give the syn ‐addition products of type 5 . On hydrolysis, these yield besides methyl L ‐valinate ( 6 ) and small amounts of the dipeptide ester 8 the (2 R ,3 S )‐ threo ‐serine methyl esters of type 7 . Chloramphenicol ( 9 ) can be obtained from the ester ent ‐ 7d by known methodology.