title: Asymmetric synthesis of cyclic indole aminals via 1,3-stereoinduction.
abstract: A general and efficient asymmetric synthesis of cyclic indoline aminals was developed with a high level of 1,3-stereoinduction through a dynamic crystallization-driven condensation. Dehydrogenation of the indoline aminals with potassium permanganate produced the corresponding cyclic indole aminals in high yields and excellent enantioselectivities. This general methodology was successfully applied to the synthesis of a wide variety of chiral cyclic indoline aminals and indole aminals with aromatic and aliphatic functional groups.
authors.affiliation: Department of Process Chemistry, Merck Research Laboratories, Merck & Co., Inc. , Rahway, New Jersey 07065, United States.
authors.forename: Hongmei
authors.initials: H
authors.lastname: Li
authors.forename: Cheng-yi
authors.initials: CY
authors.lastname: Chen
authors.forename: Hoa
authors.initials: H
authors.lastname: Nguyen
authors.forename: Ryan
authors.initials: R
authors.lastname: Cohen
authors.forename: Peter E
authors.initials: PE
authors.lastname: Maligres
authors.forename: Nobuyoshi
authors.initials: N
authors.lastname: Yasuda
authors.forename: Ian
authors.initials: I
authors.lastname: Mangion
authors.forename: Ilia
authors.initials: I
authors.lastname: Zavialov
authors.forename: Mikhail
authors.initials: M
authors.lastname: Reibarkh
authors.forename: John Y L
authors.initials: JY
authors.lastname: Chung
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007211:Indoles; C057812:indoline; C030374:indole