title: Diversity-oriented synthesis based on the DPPP-catalyzed mixed double-Michael reactions of electron-deficient acetylenes and β-amino alcohols.
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.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA.
authors.forename: Yi Chiao
authors.initials: YC
authors.lastname: Fan
authors.forename: Ohyun
authors.initials: O
authors.lastname: Kwon
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*; D011407:Propane / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000480:Alkynes; D000605:Amino Alcohols; D010080:Oxazoles; D010720:Phosphines; C064210:oxazolidine; C467590:1,3-bis(diphenylphosphino)propane; C044646:phosphine; D011407:Propane