Palladium-catalyzed regioselective hydrodebromination of dibromoindoles: application to the enantioselective synthesis of indolodioxane U86192A.
A novel approach to the selective preparation of 4-bromoindoles was developed via Pd(OAc)(2)/rac-BINAP catalytic reactions. A variety of 4,6-dibromoindoles were transformed to 4-bromoindoles with high regioselectivity. This methodology, along with C-N and C-O bond-forming reactions developed in our laboratory, was applied to the enantioselective synthesis of indolodioxane U86192A, an antihypertensive agent.
Chae
Junghyun
J
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Buchwald
Stephen L
SL
D000959:Antihypertensive Agents / Q000138:chemical synthesis*; D001965:Bromides / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000959:Antihypertensive Agents; D001965:Bromides; D007211:Indoles; C489891:U86192A; D010165:Palladium; D001966:Bromine