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Trading N and O. Part 3: Synthesis of 1,2,3,4-tetrahydroisoquinolines from alpha-hydroxy-beta-amino esters

Abstract:

All rights reserved.A range of enantiopure 1,2,3,4-tetrahydroisoquinolines have been prepared directly from α-hydroxy-β-amino esters. Activation of the α-hydroxy group upon treatment with Tf2O and 2,6-di-tert-butyl-4-methylpyridine promotes aziridinium formation, which is then followed by rupture of the C(3)-N bond and Friedel-Crafts alkylation-type cyclisation of an N-benzyl moiety onto the resultant benzylic carbenium ion. The nature of the N-protecting group was varied and it was found tha...

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

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Publisher copy:
10.1016/j.tet.2016.03.008

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Fletcher, AM More by this author
Kennedy, MS More by this author
Roberts, PM More by this author
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Publisher:
Elsevier Ltd. Publisher's website
Journal:
Tetrahedron Journal website
Volume:
72
Issue:
17
Pages:
2139-2163
Publication date:
2016-03-02
Acceptance date:
2016-03-01
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
URN:
uuid:3890bf5a-c399-4816-aae0-5939fc2273d4
Source identifiers:
612266
Local pid:
pubs:612266

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