88088-52-2

Upstream product

• 591-50-4 iodobenzene 
• 79705-07-0 (3S,4R)-4-Methyl-hex-5-en-1-yn-3-ol 
• 79705-07-0 (3R,4R)-4-Methyl-hex-5-en-1-yn-3-ol 
• 79705-05-8 (E)-1-(prop-2-yn-1-yloxy)but-2-ene 
• 88088-42-0 {3-[((E)-But-2-enyl)oxy]-prop-1-ynyl}-trimethyl-silane 
• 88088-48-6 (3S,4R)-4-Methyl-1-trimethylsilanyl-hex-5-en-1-yn-3-ol 

Downstream Products

• 88088-55-5 (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhex-5-enol 
• 88088-54-4 (E)-(3S^*,4R^*)-3-methoxy-4-methyl-1-phenylhexa-1,5-diene 
• 88088-55-5 (E)-(3S,4S)-4-Methoxy-3-methyl-6-phenyl-hex-5-en-1-ol 
• 88155-83-3 methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate 
• 88088-56-6 (E)-(3R,4S)-4-Methoxy-3-methyl-6-phenyl-hex-5-enoic acid 
• 84118-90-1 (syn)-(E)-3-hydroxy-4-methyl-1-phenyl-1,5-hexadiene 

Relevant academic research and scientific papers

-WITTIG SIGMATROPIC REARRANGEMENT OF CROTYL PROPARGYL ETHER SYSTEM; AN EMERGING TOOL FOR CONTROL OF ACYCLIC STEREOCHEMISTRY

The -Wittig rearrangement of properly designated (E)- and (Z)-crotyl propargyl ether system has been shown to exhibit a remarkably high degree of threo- and erythro-selection, respectively, and the stereochemical outcomes are discussed on mechanistic grounds.Some useful transformations of the rearrangement product are also described within the context of the formal total synthesis of (+/-)-oudemansin.Further, the high level of diastereoselection is maintained in the reaction of the α-methylcrotyl counterparts, together with the exclusive formation of the (E)-olefinic bond.

ENHANCEMENT OF ERYTHRO-SELECTIVITY IN THE -WITTIG REARRANGEMENT OF CROTYL PROPARGYL ETHER SYSTEM AND ITS USE IN THE STEREOCONTROLLED FORMAL SYNTHESIS OF (+/-)-OUDEMANSIN

The -Wittig variant of (Z)-crotyl ether involving trimethylsilylethynyl (or 1-propynyl) group as the key substituent on the carbanion terminus exhibits an exceptionally high level of erythro-selection, and its synthetic potential is illustrated in th