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Molecules 2011, 16(5), 3802-3825; doi:10.3390/molecules16053802
Article

Diversity-Oriented Synthesis Based on the DPPP-Catalyzed Mixed Double-Michael Reactions of Electron-Deficient Acetylenes and β-Amino Alcohols

 and *
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA
* Author to whom correspondence should be addressed.
Received: 6 April 2011 / Revised: 29 April 2011 / Accepted: 5 May 2011 / Published: 5 May 2011
(This article belongs to the Special Issue Diversity Oriented Synthesis)
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Abstract

In this study, we prepared oxizolidines through 1,3-bis(diphenylphosphino)-propane (DPPP)–catalyzed mixed double-Michael reactions of b-amino alcohols with electron-deficient acetylenes. These reactions are very suitable for the diversity-oriented parallel syntheses of oxizolidines because: (i) they are performed under mild metal-free conditions and (ii) the products are isolated without complicated work-up. To demonstrate the applicability of mixed double-Michael reactions for the preparation of five-membered-ring heterocycles, we prepared 60 distinct oxazolidines from five β-amino alcohols and 12 electron-deficient acetylenes. We synthesized 36 of these 60 oxazolidines in enantiomerically pure form from proteinogenic amino acid–derived β-amino alcohols.
Keywords: phosphine catalysis; Michael reaction; oxazolidines; β-amino alcohols; acetylenes phosphine catalysis; Michael reaction; oxazolidines; β-amino alcohols; acetylenes
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Fan, Y.C.; Kwon, O. Diversity-Oriented Synthesis Based on the DPPP-Catalyzed Mixed Double-Michael Reactions of Electron-Deficient Acetylenes and β-Amino Alcohols. Molecules 2011, 16, 3802-3825.

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