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

作者：Fan Yi Chiao; Kwon Ohyun^*

来源：Molecules, 2011, 16(5): 3802-3825.

DOI：10.3390/molecules16053802

• phosphine catalysis
• Michael reaction
• oxazolidines
• beta-amino alcohols
• acetylenes

In this study, we prepared oxizolidines through 1,3-bis(diphenylphosphino)propane (DPPP)-catalyzed mixed double-Michael reactions of beta-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 beta-amino alcohols and 12 electron-deficient acetylenes. We synthesized 36 of these 60 oxazolidines in enantiomerically pure form from proteinogenic amino acid-derived beta-amino alcohols.

• 出版日期2011-5