Stereoselective Synthesis of iso-Dolaproine via Dynamic Kinetic Resolution

Stereoselective Synthesis of iso-Dolaproine via Dynamic Kinetic Resolution

An efficient multigram-scale synthesis of optically pure Boc-(2S,3R,4S)-iso-dolaproine is reported using dynamic kinetic resolution (DKR). The catalytic asymmetric hydrogenation of ethyl (4S)-3-(2‘-pyrrolidinyl)-3-oxo-2-methyl propanoate hydrochloride using in situ generated Ru[(S)-MeO-BIPHEP]Br2 ca...

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Veröffentlicht in:Organic letters 2001-06, Vol.3 (12), p.1909-1912
Hauptverfasser: Lavergne, Damien, Mordant, Céline, Ratovelomanana-Vidal, Virginie, Genet, Jean-Pierre
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Catalysis
Kinetics
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Stereoisomerism
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Zusammenfassung:An efficient multigram-scale synthesis of optically pure Boc-(2S,3R,4S)-iso-dolaproine is reported using dynamic kinetic resolution (DKR). The catalytic asymmetric hydrogenation of ethyl (4S)-3-(2‘-pyrrolidinyl)-3-oxo-2-methyl propanoate hydrochloride using in situ generated Ru[(S)-MeO-BIPHEP]Br2 catalyst affords the anti β-hydroxy α-methyl ester quantitatively. The two new stereogenic centers are simultaneously controlled with high diastereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015955g