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Rapid stereoselective syntheses of heteroarene-fused azacycles via diastereoselective conjugate addition of heteroaryl substituted lithium amides

Abstract:
Conjugate addition of heteroaryl substituted lithium amides to a range of α,β-unsaturated esters followed by in situ enolate oxidation with (–)-(camphorsulfonyl)oxaziridine gave the corresponding α-hydroxy-β-amino esters. Subsequent Friedel-Crafts type cyclisation of these α-hydroxy-β-amino esters gave a range of heteroarene-fused azacycles in good yields and high diastereoselectivities.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.3987/COM-18-S(F)59

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Magdalen College
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
St Catherine's College
Role:
Author


Publisher:
Japan Institute of Heterocyclic Chemistry
Journal:
Heterocycles More from this journal
Volume:
99
Issue:
2
Pages:
919-941
Publication date:
2018-12-05
DOI:
EISSN:
1881-0942
ISSN:
0385-5414


Pubs id:
pubs:1039667
UUID:
uuid:843bf7cb-31f1-4dcf-b0a0-784f29fc66a0
Local pid:
pubs:1039667
Source identifiers:
1039667
Deposit date:
2019-08-10

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