Synthesis of chiral 3E,5E-octadiene-1,2R-7R,8-tetraol frameworks by means of palladium(II)-promoted hetero-Claisen rearrangement: Mechanistic aspect

Tetrahedron

Volumn 52, Issue 44, 1996, Pages 13919-13932

  Saito, Seiki ^a   Kuroda, Akiyoshi ^a   Matsunaga, Hiroshi ^a   Ikeda, Shushiro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; POLYOL;

ARTICLE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030605047     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00854-X     Document Type: Article

References (23)

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9. 3).
10. 6(7) one must be responsible. The similar effect has been proposed for the rearrangements of 3-acetoxy-(1E,4Z)-dienes shown in eq (5): the rate of rearrangement involving (E)-allylic acetate moiety might be decelerated because of the π-σ* hyperconjugative electron withdrawing inductive effect of a TBSO-group attached to it (ref. 4(c)).
11. (8) The carbonates gave much better results as compared with those obtained in the case of acetates in terms of the amount of byproducts and chemical yield.
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