- 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...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1021/ol9004118
-
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- 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
- Language:
- English
- Keywords:
- Copyright date:
- 2009
Journal article
A tandem conjugate addition/cyclization protocol for the asymmetric synthesis of 2-aryl-4-aminotetrahydroquinoline-3-carboxylic acid derivatives.
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