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Simple Chiral Diaminobinaphthyl Dilithium Salts for Intramolecular Catalytic Asymmetric Hydroamination of Amino‐1,3‐dienes
Author(s) -
Deschamp Julia,
Olier Clarisse,
Schulz Emmanuelle,
Guillot Régis,
Hannedouche Jérôme,
Collin Jacqueline
Publication year - 2010
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.201000302
Subject(s) - chemistry , hydroamination , enantioselective synthesis , dilithium , methyllithium , intramolecular force , lithium amide , lithium (medication) , catalysis , amide , tetramethylethylenediamine , diamine , medicinal chemistry , organic chemistry , stereochemistry , deprotonation , ion , medicine , endocrinology
Simple and easily accessible chiral lithium amide salts are reported as efficient (pre)catalysts for the diastereo‐ [up to ( E : Z )=92:8] and enantioselective [up to 72% ee ( E )] hydroamination/cyclisation of conjugated primary aminodienes. These chiral lithium salts are straightforwardly prepared by in situ combination of an N ‐substituted ( R )‐(+)‐1,1′‐binaphthyl‐2,2′‐diamine ligand and a commercial methyllithium solution. Information on the solid‐state structure of these salts was obtained by X‐ray analysis of a single crystal.