Abstract
A novel Michael-initiated ring closure reacton involving allylic chlorosulfone (2) and γ-alkoxy-α,β-ynoates to afford 4- methylenecyclopentenecarboxylates is reported, while with γ-alkylynoates no reaction occurred. With chiral phenyl ynoates 4, the reaction proceeds by 1,3-asymmetric induction and leads further to a nonracemic annulated α,β- butenolide (7). (C) 2000 Elsevier Science Ltd.
Original language | English |
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Pages (from-to) | 5583-5587 |
Number of pages | 5 |
Journal | Tetrahedron Letters |
Volume | 41 |
Issue number | 29 |
DOIs | |
State | Published - 15 Jul 2000 |
Bibliographical note
Funding Information:The authors wish to thank the US–Israel Science Foundation and the Marcus Center for Pharmaceutical and Medicinal Chemistry at Bar-Ilan University for financial support, and Dr. Hugo E. Gottlieb for his valuable help in NMR analysis.
Keywords
- Asymmetric induction
- Butenolides
- Cyclopentenecarboxylates
- Lithium ion chelation
- Michael reactions