Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 7, Pages 1374-1382Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300148
Keywords
asymmetric synthesis; chiral diene; cycloisomerization; ene-ynamides; rhodium
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Funding
- MEXT, Japan
- UBE Foundation
- Grants-in-Aid for Scientific Research [25105730] Funding Source: KAKEN
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The rhodium-catalyzed asymmetric cycloisomerization of heteroatom-bridged 1,6-ene-ynamides proceeded to give high yields of functionalized 3-aza- and oxabicyclo[4.1.0]heptene derivatives with high enantioselectivity, which was achieved by use of a rhodium/chiral diene catalyst. The 1,6-ene-ynamides substituted with 2-oxazolidinone and 2-azetidinone moieties at the alkyne terminus were found to display high reactivity towards the rhodium/chiral diene catalyst, where the chelate coordination of the alkyne moiety and the carbonyl oxygen of the ene-ynamides might be responsible for the high catalytic activity.
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