Journal article icon

Journal article

Synthesis of (E)-4-methylhexa-3,5-dien-1-ol and its Diels-Alder reaction with thioester dienophiles: a short enantioselective synthesis of bicyclic lactones

Abstract:

The preparation of (E)-4-methylhexa-3,5-dien-1-ol has been achieved in a single step from 3-methylpenta-1,4-diene via deprotonation with BuLi, alkylation with paraformaldehyde, and metal counterion exchange in situ to promote oxy-anion accelerated [1,3]-sigmatropic shift. This alcohol is shown to undergo intermolecular Diels-Alder reaction with 3-isopropyl acrylate thioesters; the so-formed exclusive endo-adduct may then be closed to the bicyclic lactone, the product of formal intramolecular ...

Expand abstract
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

Actions


Access Document


Files:
Publisher copy:
10.1002/ejoc.201700900

Authors


More by this author
Department:
Brasenose College
Role:
Author
Publisher:
Wiley Publisher's website
Journal:
European Journal of Organic Chemistry Journal website
Volume:
2017
Issue:
33
Pages:
4916–4921
Publication date:
2017-07-14
Acceptance date:
2017-07-14
DOI:
EISSN:
1099-0690
ISSN:
1434-193X
Pubs id:
pubs:709058
URN:
uri:18a4954f-83b5-43dc-91e0-b63500fa4bf4
UUID:
uuid:18a4954f-83b5-43dc-91e0-b63500fa4bf4
Local pid:
pubs:709058

Terms of use


Metrics


Views and Downloads






If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP