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.
Funding
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.
Funders | Funder number |
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Marcus Center for Pharmaceutical and Medicinal Chemistry at Bar-Ilan University | |
Israel Science Foundation |
Keywords
- Asymmetric induction
- Butenolides
- Cyclopentenecarboxylates
- Lithium ion chelation
- Michael reactions