Recent advances in transition metal-catalyzed or -mediated cyclization
of 2,3-allenoic acids: New methodologies for the synthesis of butenolides
S. Ma
State Key Laboratory of Organometallic Chemistry,
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences,
354 Fenglin Lu, Shanghai 200032, China
Abstract: The cyclization reactions of 2,3-allenoic acids or
their salts with optically active bases affording butenolides are discussed.
Two reaction pathways were observed: (1) intermolecular carbometallation-intramolecular
allylation; (2) cyclic oxymetallation-reductive elimination. High efficiency
of chirality transfer was realized with the latter case.
*Plenary and invited lectures presented at the 12th
International Symposium on Organometallic Chemistry Directed Towards
Organic Synthesis (OMCOS-12), Toronto, Ontario, Canada, 6-10 July 2003.
Other lectures are published in this issue, pp.
453-695.
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