Synthesis of Chiral 2‐Hydroxy‐1‐methylpropanoates by Rhodium‐Catalyzed Stereoselective Hydrogenation of α‐(Hydroxymethyl)‐acrylate Derivatives | Zendy

Holz Jens | Zendy; Schäffner Benjamin | Zendy; Zayas Odalys | Zendy; Spannenberg Anke | Zendy; Börner Armin | Zendy

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Synthesis of Chiral 2‐Hydroxy‐1‐methylpropanoates by Rhodium‐Catalyzed Stereoselective Hydrogenation of α‐(Hydroxymethyl)‐acrylate Derivatives

Author(s) -

Holz Jens,

Schäffner Benjamin,

Zayas Odalys,

Spannenberg Anke,

Börner Armin

Publication year - 2008

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.200800525

Subject(s) - chemistry , stereoselectivity , rhodium , kinetic resolution , catalysis , hydroxymethyl , organic chemistry , asymmetric hydrogenation , acrylate , enantioselective synthesis , stereochemistry , medicinal chemistry , copolymer , polymer

The synthesis of chiral 3‐hydroxy‐2‐methylpropanoic acid esters (e.g., “Roche ester” 3a ) based on the rhodium‐catalyzed stereoselective hydrogenation of Baylis–Hillman reaction products was investigated. Full conversions and enantioselectivities of up to 99% at a substrate/catalyst ratio of up to 500/1 were achieved by application of bisphospholanes of the cat AS ium M series as ancillary ligands. An interesting kinetic resolution was observed by the diastereoselective hydroxy‐directed hydrogenation of related racemic β‐branched precursors affording mainly anti ‐isomers with up to 96%ee.

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