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Issue 74, 2017
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Effect of protic additives in Cu-catalysed asymmetric Diels–Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids

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Abstract

The pronounced beneficial effect of a precise amount of protic additive in an enantioselective Cu-catalysed Diels–Alder reaction is reported. This reaction, which employs a cyclic alkylidene β-ketoester as a dienophile, represents one of the first examples of a transformation where these extremely versatile, though highly unstable reaction partners participate effectively in catalytic asymmetric cycloaddition with a functionalised diene. The cycloadduct was used as an intermediate towards the synthesis of magellanine-type Lycopodium alkaloids featuring a Stille cross-coupling of a highly congested enol triflate and a unique Meinwald rearrangement/cyclopropanation sequence.

Graphical abstract: Effect of protic additives in Cu-catalysed asymmetric Diels–Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids

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Article information


Submitted
14 Aug 2017
Accepted
28 Aug 2017
First published
29 Aug 2017

Chem. Commun., 2017,53, 10291-10294
Article type
Communication

Effect of protic additives in Cu-catalysed asymmetric Diels–Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids

V. N. G. Lindsay, R. A. Murphy and R. Sarpong, Chem. Commun., 2017, 53, 10291
DOI: 10.1039/C7CC06367A

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