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Conjugate addition of lithium N-phenyl-N-(α-methylbenzyl)amide: application to the asymmetric synthesis of (R)-(-)-angustureine.

Abstract:
The conjugate addition of lithium (R)-N-phenyl-N-(α-methylbenzyl)amide to a range of α,β-unsaturated 4-methoxyphenyl esters proceeds with excellent levels of diastereoselectivity to give the corresponding β-amino esters in good yield and as single diastereoisomers (>99:1 dr). The synthetic utility of this methodology has been demonstrated via the short and concise asymmetric synthesis of the tetrahydroquinoline alkaloid (R)-(-)-angustureine in six steps and 32% overall yield from commercially available oct-2-enoic acid.
Publication status:
Published

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Publisher copy:
10.1021/ol200625h

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic letters
Volume:
13
Issue:
10
Pages:
2544-2547
Publication date:
2011-05-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:3824b2d9-f092-4786-8792-b6ced82648b0
Source identifiers:
134940
Local pid:
pubs:134940

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