Tetrahedron 2018-03-31

Direct enolization chemistry of 7-azaindoline amides: A case study of bis(tetrahydrophosphole)-type ligands

Zhao Li, Hidetoshi Noda, Naoya Kumagai, Masakatsu Shibasaki

Index: 10.1016/j.tet.2018.03.073

Full Text: HTML

Abstract

7-Azaindoline amides are particularly useful in direct enolization chemistry due to their facilitated enolization in soft Lewis acid/Brønsted base cooperative catalysis. The Cu(I) complex of (R,R)-Ph-BPE, a bis(tetrahydrophosphole)-type chiral bisphosphine ligand, exhibits consistently high catalytic performance and stereoselectivity irrespective of the nature of the α-substituent of the amides. Unexpectedly, however, alkyl-substituted bis(tetrahydrophosphole)-type ligands have substantially inferior catalytic performance. Evaluation of the optimized structures of Cu(I)/amide and Cu(I)/enolate complexes provided clues to dissecting the diverted reaction outcomes.

Latest Articles:

Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C─N coupling reaction of aryl halides and α-aminoamides

2018-04-11

[10.1016/j.tet.2018.03.003]

A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs

2018-04-11

[10.1016/j.tet.2018.04.022]

Chemoselectivity in the Kosugi-Migita-Stille coupling of bromophenyl triflates and bromo-nitrophenyl triflates with (ethenyl)tributyltin

2018-04-10

[10.1016/j.tet.2018.02.051]

Process design methodology for organometallic chemistry in continuous flow systems

2018-04-07

[10.1016/j.tet.2018.04.020]

Substrate engineering: Effects of different N-protecting groups in the CAL-B-catalysed asymmetric O-acylation of 1-hydroxymethyl-tetrahydro-β-carbolines

2018-04-07

[10.1016/j.tet.2018.04.012]

More Articles...