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Asymmetric Synthesis of Acyclic Amines Through Zr‐ and Hf‐Catalyzed Enantioselective Alkylzinc Reagents to Imines
Author(s) -
Akullian Laura C.,
Porter James R.,
Traverse John F.,
Snapper Marc L.,
Hoveyda Amir H.
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404319
Subject(s) - chemistry , enantioselective synthesis , reagent , amine gas treating , catalysis , combinatorial chemistry , lewis acids and bases , organic chemistry
Abstract Readily available chiral amino acid‐based ligands are used in metal‐catalyzed additions of alkylzinc reagents to various aromatic and aliphatic imines; the desired amine products are formed efficiently and in high levels of optical purity. In cases where the more Lewis acidic Zr salts afford lower efficiency, Hf‐based catalysts deliver significantly higher yields with similar enantioselectivities. Critical structural features of the N‐activating groups as well as the optimal chiral ligands are discussed. A mechanistic working model is presented to rationalize the existing data and to serve as a predictive tool.