Lewis Acid Activated Synthesis of Highly Substituted Cyclopentanes by the N-Heterocyclic Carbene Catalyzed Addition of Homoenolate Equivalents to Unsaturated Ketoesters

A great team: Cyclopentanes with four contiguous stereogenic centers were assembled with excellent diastereo‐ and enantioselectivity from simple β,γ‐unsaturated α‐ketoesters and enals in a reaction catalyzed by an N‐heterocyclic carbene (NHC) and mediated by a titanium(IV) Lewis acid (see scheme). T...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 50; no. 7; pp. 1678 - 1682
Main Authors Cohen, Daniel T, Cardinal-David, Benoit, Scheidt, Karl A
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 11.02.2011
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
asymmetric catalysis
asymmetric synthesis
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Esters
Heterocyclic Compounds - chemistry
homoenolates
Lewis acids
Lewis Acids - chemistry
Methane - analogs & derivatives
Methane - chemistry
N-heterocyclic carbenes
Physical Sciences
Science & Technology
Stereoisomerism
Titanium - chemistry
homoenolates
DIELS-ALDER REACTIONS
ENANTIOSELECTIVE SYNTHESIS
ALPHA,BETA-UNSATURATED ALDEHYDES
Lewis acids
EFFICIENT SYNTHESIS
asymmetric catalysis
GAMMA-BUTYROLACTONES
NUCLEOPHILIC CARBENES
asymmetric synthesis
METHYL (E)-4-METHOXY-2-OXO-3-BUTENOATE
FACIAL SELECTIVITY
STEREOSELECTIVE-SYNTHESIS
CONJUGATE ADDITIONS
N-heterocyclic carbenes
Online AccessGet full text

Cover

More Information
Summary:A great team: Cyclopentanes with four contiguous stereogenic centers were assembled with excellent diastereo‐ and enantioselectivity from simple β,γ‐unsaturated α‐ketoesters and enals in a reaction catalyzed by an N‐heterocyclic carbene (NHC) and mediated by a titanium(IV) Lewis acid (see scheme). The presence of a Lewis acid was essential for the desired transformation to occur.
Bibliography:http://dx.doi.org/10.1002/anie.201005908
istex:1C0E5CCBB7D94779448DA87D497B8C9743E37AA8
Financial support was generously provided by the NIH (NIGMS RO1 GM73072), Amgen, AstraZeneca, GlaxoSmithKline, and a GAANN (Graduate Assistance in Areas of Nation Need) fellowship to D.T.C. FQRNT (Fonds Québécois de la Recherche sur la Nature et les Technologies) is also gratefully acknowledged for a postdoctoral fellowship to B.C.-D. We thank John M. Roberts (NU) for assistance with X-ray crystallography.
NIH - No. NIGMS RO1 GM73072
ArticleID:ANIE201005908
ark:/67375/WNG-24GH70N3-7
Financial support was generously provided by the NIH (NIGMS RO1 GM73072), Amgen, AstraZeneca, GlaxoSmithKline, and a GAANN (Graduate Assistance in Areas of Nation Need) fellowship to D.T.C. FQRNT (Fonds Québécois de la Recherche sur la Nature et les Technologies) is also gratefully acknowledged for a postdoctoral fellowship to B.C.‐D. We thank John M. Roberts (NU) for assistance with X‐ray crystallography.
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201005908