Unprecedented stereochemical control in the Claisen rearrangement of allyl vinyl ethers using organoaluminum reagents

…, K Nonoshita, H Banno, H Yamamoto

Index: Maruoka, Keiji; Nonoshita, Katsumasa; Banno, Hiroshi; Yamamoto, Hisashi Journal of the American Chemical Society, 1988 , vol. 110, # 23 p. 7922 - 7924

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Citation Number: 54

Abstract

Four-bond IH-IH coupling was important in determining the structure of unit G, including the placement of a hydroxyl group on C-24 (COSY shows cross peaks from the OH on C-24 to H- 25 and H3-36), and in connecting a methyl group to C-18 in unit F. Vicinal coupling constants indicated that (1) the geometries of the AI1 and Azo double bonds were cis and trans, respectively,(2) hydroxyl groups were attached to C-15, C-16, and C-47, and (3) a ...