title: Michael addition of amines and thiols to dehydroalanine amides: a remarkable rate acceleration in water.
abstract: In water, the rate of Michael addition of amines and thiols to dehydroalanine amides was greatly accelerated, leading to shorter reaction times and higher yields. The scope of the new conditions was tested with a range of amines, thiols, and dehydroalanine amides. The ease and efficiency of this method provides an attractive route to the synthesis of natural and unnatural amino acid derivatives.
authors.affiliation: Discovery Chemistry, The Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA. Narasimhulu.Naidu@bms.com
authors.forename: B Narasimhulu
authors.initials: BN
authors.lastname: Naidu
authors.forename: Margaret E
authors.initials: ME
authors.lastname: Sorenson
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Connolly
authors.forename: Yasutsugu
authors.initials: Y
authors.lastname: Ueda
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives*; D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D007700:Kinetics; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D000577:Amides; D000588:Amines; D013438:Sulfhydryl Compounds; D014867:Water; D000409:Alanine