Enantiopure 2-aryl-2-methyl cyclopentanones by an asymmetric chelation-controlled Heck reaction using aryl bromides: increased preparative scope and effect of ring size on reactivity and selectivity

Quaternary 2-aryl-2-methyl cyclopentanones were obtained in 85–94% ee via Pd(0)-catalyzed chelation-controlled asymmetric arylation of a cyclopentenyl ether with aryl bromides and subsequent hydrolysis. Two new cyclohexenyl ethers were synthesized and evaluated as Heck substrates with both aryl iodi...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry 2008-05, Vol.19 (9), p.1120-1126
Main Authors: Datta, Gopal K., Nordeman, Patrik, Dackenberg, Jakob, Nilsson, Peter, Hallberg, Anders, Larhed, Mats
Format: Article
Language:English
Subjects:
FARMACI
PHARMACY
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Quaternary 2-aryl-2-methyl cyclopentanones were obtained in 85–94% ee via Pd(0)-catalyzed chelation-controlled asymmetric arylation of a cyclopentenyl ether with aryl bromides and subsequent hydrolysis. Two new cyclohexenyl ethers were synthesized and evaluated as Heck substrates with both aryl iodides and bromides under different reaction conditions. Arylations of the six-membered vinyl ether 1-methyl-2-( S)-(cyclohex-1-enyloxymethyl)-pyrrolidine with aryl bromides were achieved with t-Bu 3P-promoted palladium catalysis using either classical or microwave heating. Isolated Heck products were also obtained in high diastereoselectivities (94–98% de).
ISSN:0957-4166
1362-511X
1362-511X
DOI:10.1016/j.tetasy.2008.04.004