Synthetic Applications (II) of the Tandem [2,3]-Wittig-Anionic Oxy-Cope Rearrangement: Stereoselective Trisubstituted δ-Lactone and Tetrahydropyran Synthesis
摘要:
Di-and trisubstituted delta-lactones have been prepared by stereoselective iodolactonisation and phenylselenolactonisation of delta,epsilon-unsaturated carboxylic acids. The acyclic stereochemistry of the acids arises from highly stereoselective tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of cinnamyl ethers with potassium hydride and 18-crown-6 in THF to give delta,epsilon-unsaturated aldehydes. (C) 1997 Elsevier Science Ltd.
Synthetic Applications (II) of the Tandem [2,3]-Wittig-Anionic Oxy-Cope Rearrangement: Stereoselective Trisubstituted δ-Lactone and Tetrahydropyran Synthesis
摘要:
Di-and trisubstituted delta-lactones have been prepared by stereoselective iodolactonisation and phenylselenolactonisation of delta,epsilon-unsaturated carboxylic acids. The acyclic stereochemistry of the acids arises from highly stereoselective tandem [2,3]-Wittig-anionic oxy-Cope rearrangement of cinnamyl ethers with potassium hydride and 18-crown-6 in THF to give delta,epsilon-unsaturated aldehydes. (C) 1997 Elsevier Science Ltd.