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Abstract
In this study, we prepared oxizolidines through 1,3-bis(diphenylphosphino)-propane (DPPP)–catalyzed mixed double-Michael reactions of β-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.
Highlights
Because small organic heterocyclic compounds are found in most pharmaceuticals and agrochemicals and in numerous natural products, additives, modifiers, and polymers [1,2], their construction remains of great interest to the synthetic organic chemistry community
Here we report the synthesis of a library of 60 distinct oxazolidines through our mixed double-Michael strategy
The β-amino alcohol pro-nucleophiles that we used in the mixed double-Michael reactions were derived from natural L-amino acids and racemic cyclohexene oxide
Summary
Because small organic heterocyclic compounds are found in most pharmaceuticals and agrochemicals and in numerous natural products, additives, modifiers, and polymers [1,2], their construction remains of great interest to the synthetic organic chemistry community. Based on previously reported mixed double-Michael reactions [30,31], we knew that oxazolidines could be prepared from amino acid–derived pro-nucleophiles and electron-deficient acetylenes using DPPP as the catalyst. With such precedents in mind, here we expanded the reaction scope of the mixed double-Michael reaction to incorporate. Enantiomerically pure oxazolidines can be used as chiral auxiliaries to induce asymmetry in organic reactions [40,41,42,43,44,45]
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