Journal article
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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Bibliographic Details
- Journal:
- Organic letters
- Volume:
- 13
- Issue:
- 10
- Pages:
- 2544-2547
- Publication date:
- 2011-05-01
- DOI:
- EISSN:
-
1523-7052
- ISSN:
-
1523-7060
- Source identifiers:
-
134940
Item Description
- Language:
- English
- Keywords:
- Pubs id:
-
pubs:134940
- UUID:
-
uuid:3824b2d9-f092-4786-8792-b6ced82648b0
- Local pid:
- pubs:134940
- Deposit date:
- 2012-12-19
Terms of use
- Copyright date:
- 2011
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