Highly Enantioselective Synthesis of 1,2-Amino Alcohol Derivatives via Proline-Catalyzed Mannich Reaction

Abstract

Here we report a new catalytic asymmetric synthesis of oxazolidin-2-ones 4 and Cbz-protected 1,2-amino alcohols 5. Our sequence is based on the chemistry of previously unknown 5-acylox­y-oxazolidin-2-ones, which are obtained via proline-catalyze­d direct asymmetric three-component Mannich reaction and Baeyer-Villiger oxidation.

Key words

multicomponent reactions - organocatalysis - oxa­zolidinones - aminoalcohols

References

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  MCPBA was less efficient in these reactions.

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1

New Address: Max-Plank-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany.
E-mail: [e-mail]

12

Aliphatic amino alcohol 5d was obtained enantiomerically pure after recrystallization of an intermediate, see ref. [1]