A facile synthetic method of α-quaternary-β,γ-unsaturated aldehydes via the stereoselective 1,4-elimination and α-regioselective Ferrier reaction |
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Authors: | Eiji Tayama Ryo Hashimoto |
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Institution: | Graduate School of Science and Technology, Niigata University, Niigata 950-2181, Japan |
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Abstract: | The 1,4-elimination reaction of 2-substituted-(2Z)-4-methoxy-O-alkenyl acetals with n-butyllithium is shown to afford the 2-substituted-(1Z,3E)-O-1,3-dienyl acetals in high stereoselectivities. The Ferrier reaction of the O-1,3-dienyl acetals thus obtained provides the corresponding α-quaternary-β,γ-unsaturated aldehydes in excellent yields with high α-regioselectivities. |
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Keywords: | 1 4-Elimination 1 3-Dienyl acetals 1-Alkoxy-1 3-dienes Ferrier reaction α-Quaternary-β γ-unsaturated aldehydes |
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