Enantio- and Diastereoselective Catalytic Mannich-Type Reaction of a Glycine Schiff Base Using a Chiral Two-Center Phase-Transfer Catalyst

Optically active α,β‐diamino acids are prepared under asymmetric phase‐transfer reaction conditions from a glycine Schiff base and N‐protected imines with a tartrate‐derived diammonium salt (TaDiAS) as the phase‐transfer catalyst (see scheme; Boc=tert‐butoxycarbonyl). Chemoselective deprotection of...

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Veröffentlicht in:Angewandte Chemie International Edition 2005-07, Vol.44 (29), p.4564-4567
Hauptverfasser: Okada, Akihiro, Shibuguchi, Tomoyuki, Ohshima, Takashi, Masu, Hyuma, Yamaguchi, Kentaro, Shibasaki, Masakatsu
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Sprache:eng
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Zusammenfassung:Optically active α,β‐diamino acids are prepared under asymmetric phase‐transfer reaction conditions from a glycine Schiff base and N‐protected imines with a tartrate‐derived diammonium salt (TaDiAS) as the phase‐transfer catalyst (see scheme; Boc=tert‐butoxycarbonyl). Chemoselective deprotection of the N atoms allows straightforward transformations of the α,β‐diamino acid products to be carried out.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200500927