title: Chiral aminophosphines as catalysts for enantioselective double-Michael indoline syntheses.
abstract: The bisphosphine-catalyzed double-Michael addition of dinucleophiles to electron-deficient acetylenes is an efficient process for the synthesis of many nitrogen-containing heterocycles. Because the resulting heterocycles contain at least one stereogenic center, this double-Michael reaction would be even more useful if an asymmetric variant of the reaction were to be developed. Aminophosphines can also facilitate the double-Michael reaction and chiral amines are more readily available in Nature and synthetically; therefore, in this study we prepared several new chiral aminophosphines. When employed in the asymmetric double-Michael reaction between ortho-tosylamidophenyl malonate and 3-butyn-2-one, the chiral aminophosphines produced indolines in excellent yields with moderate asymmetric induction.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA.
authors.forename: San N
authors.initials: SN
authors.lastname: Khong
authors.forename: Ohyun
authors.initials: O
authors.lastname: Kwon
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008314:Malonates / Q000737:chemistry; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000588:Amines; D002074:Butanones; D007211:Indoles; D008314:Malonates; D010720:Phosphines; C057812:indoline