Addition of Benzylic and Allylic Organozinc and Grignard Reagents to Resin-Bound Imines To Provide α-Branched Secondary Amines Bearing a Wide Variety of Functional Groups. Utility in the Synthesis of β-3 Adrenergic Receptor Agonists

• Published in: Journal of combinatorial chemistry Vol. 7; no. 1; pp. 99 - 108
• Main Authors: Wu, Gang, Cai, Zhen-Wei, Bednarz, Mark S, Kocy, Octavian R, Gavai, Ashvinikumar V, Godfrey, Jollie D, Washburn, William N, Poss, Michael A, Sher, Philip M
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01-01-2005
• Subjects: Adrenergic beta-3 Receptor Agonists; Adrenergic beta-Agonists - chemical synthesis; Adrenergic beta-Agonists - chemistry; Amines - chemistry; Benzene - chemistry; Combinatorial Chemistry Techniques; Imines - chemistry; Molecular Structure; Structure-Activity Relationship; Zinc - chemistry
• ISSN: 1520-4766; 1520-4774
• DOI: 10.1021/cc0498682

Benzylic and allylic organozinc and Grignard reagents have been added to resin-bound imines to provide α-branched secondary amines. Many functional groups, including electrophilic groups, were compatible with this methodology. Three modulesa resin-bound primary amine, an aromatic aldehyde, and the organometallicwere independently varied to produce a combinatorial library of α-branched secondary amines designed as β-3 adrenergic receptor agonists.