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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 *
Received: 6 April 2011; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Fan YC, 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(5):3802-3825.

Chicago/Turabian Style

Fan, Yi Chiao; Kwon, Ohyun. 2011. "Diversity-Oriented Synthesis Based on the DPPP-Catalyzed Mixed Double-Michael Reactions of Electron-Deficient Acetylenes and β-Amino Alcohols." Molecules 16, no. 5: 3802-3825.


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