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Synthesis 1988; 1988(12): 975-977
DOI: 10.1055/s-1988-27772
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An Efficient and Stereoselective Synthesis of (E)-α-Enones via Arsonium Salts. Preparation of Key Intermediates for the Synthesis of Brassinosteroid and Prostaglandin

Yao-Zeng Huang* , Li-Lan Shi, Sao-Wei Li
  • *Shanghai Institute of Organic Chemistry, Academia Sinica, 345 Lingling Lu, Shanghai, People's Republic of China
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Publication Date:
20 August 2002 (online)

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(E)-1-Alkenyl alkyl ketones [(E)-α-Enones] are prepared in high yields and with high stereoselectivity by reaction of (2-oxoalkyl)triphenylarsonium bromides with aldehydes under solid-liquid phase-transfer conditions. Application of this methodology to the preparation of key intermediates for the synthesis of brassinosteroid and prostaglandin PGF2α is also reported.