Preparation of Stereodefined Homoallylic Amines from the Reductive Cross-Coupling of Allylic Alcohols with Imines

• Published in: Journal of organic chemistry Vol. 75; no. 23; pp. 8048 - 8059
• Main Authors: Chen, Ming Z, McLaughlin, Martin, Takahashi, Masayuki, Tarselli, Michael A, Yang, Dexi, Umemura, Shuhei, Micalizio, Glenn C
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 03.12.2010; Amer Chemical Soc
• Subjects: Aliphatic compounds; Alkenes - chemistry; Amines - chemical synthesis; Amines - chemistry; Chemistry; Chemistry, Organic; Cross-Linking Reagents - chemistry; Exact sciences and technology; Imines - chemistry; Kinetics and mechanisms; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; Propanols - chemistry; Reactivity and mechanisms; Science & Technology; Stereoisomerism; METAL-PROMOTED CYCLIZATION; ALKENES; ASYMMETRIC-SYNTHESIS; SPECTROSCOPIC PROPERTIES; MEDIATED SYNTHESIS; ENANTIOSELECTIVE ALLYLATION; ALKYNES; IN-SITU GENERATION; ZIRCONOCENE COMPLEXES; GRIGNARD-REAGENTS; Enantioselectivity; Molecular structure; Titanium complex; Haloarene; Alcohol; Chiral compound; Selectivity; Stereochemistry; Allylic compound; Organic sulfide; Chemical reduction; Stereoselectivity; Alkene; Amine; Asymmetric synthesis; Vinylic compound; Cross reaction; Reaction mechanism; Alkoxide; Aromatic compound; Metalation; Chemical synthesis; Heterocyclic compound; Halogen Organic compounds; Chemical reagent; Regioselectivity; Aliphatic compound; Chemical bond; Organometallic compound; Organic silane; Imine; Empirical model; Diastereoselectivity; Chemical coupling; Transition state; Fluorine Organic compounds; Homoallylic compound; Ethylenic compound

Regio-, diastereo-, and enantioselective coupling reactions between imines and allylic alcohols have been developed. These coupling reactions deliver complex homoallylic amine products through a convergent C−C bond forming process that does not proceed through intermediate allylic organometallic rea...