title: An Enantioselective Synthesis of an 11-β-HSD-1 Inhibitor via an Asymmetric Methallylation Catalyzed by (S)-3,3'-F2-BINOL.
abstract: An efficient asymmetric synthesis of 11-β-HSD inhibitor 1 has been accomplished in five linear steps and 53% overall yield, starting from the readily available 3-chloro-1-phenylpropan-1-one. The key feature of the synthesis includes an asymmetric methallylation of 3-chloro-1-phenylpropan-1-one catalyzed by the highly effective organocatalyst (S)-3,3'-F2-BINOL under solvent-free and metal-free conditions.
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Yongda
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Jiang-Ping
authors.initials: JP
authors.lastname: Wu
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Guisheng
authors.initials: G
authors.lastname: Li
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Keith R
authors.initials: KR
authors.lastname: Fandrick
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Joe
authors.initials: J
authors.lastname: Gao
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Zhulin
authors.initials: Z
authors.lastname: Tan
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Joe
authors.initials: J
authors.lastname: Johnson
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Wenjie
authors.initials: W
authors.lastname: Li
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Sanjit
authors.initials: S
authors.lastname: Sanyal
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Jun
authors.initials: J
authors.lastname: Wang
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Xiufeng
authors.initials: X
authors.lastname: Sun
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Jon C
authors.initials: JC
authors.lastname: Lorenz
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Sonia
authors.initials: S
authors.lastname: Rodriguez
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Jonathan T
authors.initials: JT
authors.lastname: Reeves
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Nelu
authors.initials: N
authors.lastname: Grinberg
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Heewon
authors.initials: H
authors.lastname: Lee
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Nathan
authors.initials: N
authors.lastname: Yee
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Bruce Z
authors.initials: BZ
authors.lastname: Lu
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States.
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D042842:11-beta-Hydroxysteroid Dehydrogenases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D011407:Propane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C583118:3,3'-F2-BINOL; C000611156:3-chloro-1-phenylpropan-1-one; D007659:Ketones; D009284:Naphthols; D042842:11-beta-Hydroxysteroid Dehydrogenases; D011407:Propane