Stereoselection in 5-exo radical cyclizations of polysubstituted 2- oxahex-5-enyl radicals: A systematic study of the combination substituent effect

Tetrahedron

Volumn 55, Issue 38, 1999, Pages 11465-11474

  Wille, Uta ^a   Lietzau, Lars ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

Cyclization; Diastereoselection; Radicals and radical reactions; Transition states

Indexed keywords

ETHER DERIVATIVE; NITRATE; RADICAL; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033578811     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00663-8     Document Type: Article

References (15)

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8. 2 in n-pentane/diethyl ether (3:1) at room temperature over night, no change of the ratio between both diastereoisomers was observed. However, an inversion of the stereogenic center at C(5) was possible by column chromatography using alumina (L. Lietzau, Ph.D. Thesis, University of Kiel, in preparation).
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14. [14] Formation of 1,6-cis-23a and 1,6-cis-23b may proceed through a similar mechanism as proposed in Scheme 1 for the alkynyl ethers cis/trans-1-3 with the oxygen atom in the hex-5-enyl chain being replaced by a methylene group.
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