Editing the stereochemical elements in an iridium catalyst for enantioselective allylic amination.

Abstract:

:Individual diastereomeric phosphoramidites and mixtures of diastereomeric phosphoramidites were evaluated in the iridium-catalyzed amination of allylic carbonates. The original process was conducted with a phosphoramidite ligand containing a resolved 2,2-dihydroxy-1,1-binaphthyl (BINOL) group and a diastereomerically and enantiomerically pure bis(phenethyl)amino group. Evaluation of the structure of the active catalyst and relative rates for reactions in the presence of catalysts containing diastereomeric ligands led to the identification of a phosphoramidite that provided the amination product with enantiomeric excess similar to the original, more structurally and stereochemically complex ligand and that contains a racemic BINOLate and an N-benzylphenethylamino group on phosphorus.

authors

Leitner A,Shu C,Hartwig JF

doi

10.1073/pnas.0307967101

keywords:

subject

Has Abstract

pub_date

2004-04-20 00:00:00

pages

5830-3

issue

16

eissn

0027-8424

issn

1091-6490

pii

0307967101

journal_volume

101

pub_type

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