Stereoselective Synthesis of Hydroprene and Its(2Z, 4E)-Isomer via Arsonic Ylide

Chem. J. Chinese Universities ›› 1994, Vol. 15 ›› Issue (3): 387.

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Stereoselective Synthesis of Hydroprene and Its(2Z, 4E)-Isomer via Arsonic Ylide

LIU Tian-Lin, NI Chi-You, XIE Wen-Quan, LI Zheng-Ming

Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071

Received:1993-04-09 Revised:1993-09-05 Online:1994-03-24 Published:1994-03-24

Abstract

Abstract: The key intermediate ethyl 4-bromo-3-methyl-( 2E)-butenoate 7 was obtained from ethyl 3-methyl-2-butenoate 4 by a sequence of reactions:trans-oxidation(SeO₂), reduction and bromination, Reaction of 7 and triphenylarsine gave the arsonium salt 8.Finally, reaction of 8 and dihydrocitronellal in the presence of K₂CO₃-C₂H₅OH-trace H₂O afforded hydroprene and its (2Z, 4E)-isomer in yield of 74%.The(4E)-selectivity and the partial inversion of C-2 double bond configuration happened in this reaction.

Key words: Hydroprene, Arsonic Ylide, Stereoselectivity, Synthesis

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LIU Tian-Lin, NI Chi-You, XIE Wen-Quan, LI Zheng-Ming. Stereoselective Synthesis of Hydroprene and Its(2Z, 4E)-Isomer via Arsonic Ylide[J]. Chem. J. Chinese Universities, 1994, 15(3): 387.

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Stereoselective Synthesis of Hydroprene and Its(2Z, 4E)-Isomer via Arsonic Ylide

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