Highly stereoselective 6-exo ring-closure of 5-substituted hept-6-enyl radicals

5-Substituted 7-methylthio-7-( p-tolylsulfonyl)-6-heptenyl radicals (1) and their 4-oxa derivatives cyclized in 6-exo manner with extremely high 1,2-asymmetric induction leading to trans ring-closure. Transition states for the ring closure are discussed by the experimental results and MO calculation...

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Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 51; pp. 8313 - 8316
Main Authors Ogura, Katsuyuki, Kayano, Akio, Fujino, Takeo, Sumitani, Naoko, Fujita, Makoto
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.12.1993
Elsevier
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ORGANIC-SYNTHESIS
DESIGN
CHAIN REACTIONS
CYCLIZATION
Stereoselectivity
Thioacetal oxide
Cyclization
Six membered ring
Exo stereoisomer
Saturated compound
Oxygen heterocycle
Thioketenes
Free radical reaction
Monocyclic compound
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Summary:5-Substituted 7-methylthio-7-( p-tolylsulfonyl)-6-heptenyl radicals (1) and their 4-oxa derivatives cyclized in 6-exo manner with extremely high 1,2-asymmetric induction leading to trans ring-closure. Transition states for the ring closure are discussed by the experimental results and MO calculations. Transition states of the ring-closure are discussed by the experimental results and MO calculations.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)61419-3