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Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate

Abstract:

An expeditious asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-enecarboxylate has been achieved in four steps in 42% overall yield employing as the key step a domino reaction initiated by a highly diastereoselective lithium amide 1,4-conjugate addition to a nona-2,7-diendioic diester followed by a 6-exo-trig cyclisation of the thus formed enolate. Cope elimination protocol of the cyclic adduct affords, depending on the lithium amide used, the corresponding nitro-compound or the expe...

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Publication status:
Published

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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
17
Issue:
15
Pages:
2183-2186
Publication date:
2006-09-11
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
URN:
uuid:85ae1cb0-c375-4a52-a9df-454de94b5618
Source identifiers:
110571
Local pid:
pubs:110571
Language:
English

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