Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from {alpha},{beta}-unsaturated aldehydes for enantioselective Diels-Alder reactions.

Abstract:

:The catalytic generation of chiral ester enolate equivalents from α,β-unsaturated aldehydes with chiral N-hetereocyclic carbene catalysts makes possible highly enantioselective hetero-Diels-Alder reactions. The reactions proceed under simple, mild conditions with both aliphatic and aromatic substituted enals as substrates. Previous attempts to employ these starting materials as enolate precursors gave structurally different products via catalytically generated homoenolate equivalents. Critical to the success of the enolate generation was the strength of the catalytic base used to generate the active N-heterocyclic carbene catalyst. To complement these studies, we have investigated the enolate structure using computational methods and find that it prefers conformations perpendicular to the triazolium core.

authors

Kaeobamrung J,Kozlowski MC,Bode JW

doi

10.1073/pnas.1007469107

subject

Has Abstract

pub_date

2010-11-30 00:00:00

pages

20661-5

issue

48

eissn

0027-8424

issn

1091-6490

pii

1007469107

journal_volume

107

pub_type

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