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Non-destructive Cleavage of N-Acylsultams Under Neutral Conditions: Preparation of Enantiomerically, Pure Fmoc-Protected x-Amino Acids

Authors
Oppolzer, Wolfgang
Lienard, Phillippe
Published in Helvetica Chimica Acta. 1992, vol. 75, no. 8, p. 2572-2582
Abstract Heating diastereoisomerically pure N-acylsultams 3 or 4 with allyl alcohol/Ti(OR)4 efficiently yields sultams 1 or 2 and allyl esters 5. Esters 5 are hydrolyzed under nonbasic conditions in the presence of Wilkinson's catalyst to give enantiomerically and diastereoisomerically pure carboxylic acids 7. A series of [(fluoren-9-yl)methoxy]-carbonyl-(Fmoc)-protected amino acids 14 were thus prepared from N-[N'-(Fmoc)amino]acylsultams 12.
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Other version: http://doi.wiley.com/10.1002/hlca.19920750812
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OPPOLZER, Wolfgang, LIENARD, Phillippe. Non-destructive Cleavage of N-Acylsultams Under Neutral Conditions: Preparation of Enantiomerically, Pure Fmoc-Protected x-Amino Acids. In: Helvetica Chimica Acta, 1992, vol. 75, n° 8, p. 2572-2582. https://archive-ouverte.unige.ch/unige:90947

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