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A tandem conjugate addition/cyclization protocol for the asymmetric synthesis of 2-aryl-4-aminotetrahydroquinoline-3-carboxylic acid derivatives.

Abstract:

Condensation of tert-butyl (E)-3-(2'-aminophenyl)propenoate with a range of aromatic and heteroaromatic aldehydes gives the corresponding imines as single diastereoisomers (>98% de). Addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide initiates a tandem conjugate addition/cyclization reaction to generate 2-aryl-4-aminotetrahydroquinoline-3-carboxylic acid derivatives in >98% de, >98% ee and high isolated yield. Hydrogenolysis of an N(1)-Boc protected derivative allows select...

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Publication status:
Published

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Publisher copy:
10.1021/ol9004118

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Mujtaba, N More by this author
Roberts, PM More by this author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Organic letters
Volume:
11
Issue:
9
Pages:
1959-1962
Publication date:
2009-05-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:4e5f3b1f-3ed1-468f-a021-b9669b47a81d
Source identifiers:
110564
Local pid:
pubs:110564

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