A Facile Stereocontrolled Synthesis of anti-α-(Trifluoromethyl)-β-amino Alcohols

A Facile Stereocontrolled Synthesis of anti-α-(Trifluoromethyl)-β-amino Alcohols

A short stereocontrolled preparation of anti-α-(trifluoromethyl)-β-amino alcohols is described, involving an initial CF3 transfer to cinnamaldehyde and a one-step, three-component condensation of 3,3,3-trifluorolactic aldehyde, an alkenyl (aryl) boronic acid, and an amine. Applying this methodology...

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Veröffentlicht in:Organic letters 2000-10, Vol.2 (20), p.3173-3176
Hauptverfasser: Prakash, G. K. Surya, Mandal, Mihirbaran, Schweizer, Stefan, Petasis, Nicos A, Olah, George A
Format: Artikel
Sprache:eng
Schlagworte:
Acrolein - analogs & derivatives
Acrolein - chemistry
Aldehydes - chemical synthesis
Amino Alcohols - chemical synthesis
Boronic Acids - chemistry
Ozone - chemistry
Stereoisomerism
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Zusammenfassung:A short stereocontrolled preparation of anti-α-(trifluoromethyl)-β-amino alcohols is described, involving an initial CF3 transfer to cinnamaldehyde and a one-step, three-component condensation of 3,3,3-trifluorolactic aldehyde, an alkenyl (aryl) boronic acid, and an amine. Applying this methodology to chiral 3,3,3-trifluorolactic aldehyde allowed us to generate an amino alcohol enantioselectively in 92% ee.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol000195f