862133-76-4

Upstream product

• 862133-51-5 1-(2,4,6-triisopropylphenyl)-selenyl-hex-1-yne 
• 21524-34-5 2,4,6-triisopropyl-1-bromobenzene 
• 71518-96-2 bis(2,4,6-triisopropylphenyl)diselenide 
• 130248-05-4 2,4,6-triisopropylbenzene selenenyl bromide 

Downstream Products

• 883453-91-6 (Z)-trimethyl-[2-(2,4,6-triisopropyl-phenylselanyl)-hept-2-enyl]-silane 

Relevant academic research and scientific papers

1-Iodo-1-selenoalkenes as versatile alkene 1,1-dianion equivalents. Novel connective approach towards the tetrahydropyran subunit of polycavernoside A

syn-Hydroalumination of 2,4,6-triisopropylphenylselanyl-1-alkynes with DIBAL-H followed by Al/I exchange with I2 afforded exclusively (E)-1-iodo-1-selenoalkenes in good yields. 1-Iodo-1-selenopropene 10 proved to be a convenient 1,1 dianion equivalent, leading to the stereodivergent synthesis of allylsilanes (Z)-6 and (E)-6. Adduct 3, an intermediate in the synthesis of the tetrahydropyran subunit of polycavernoside A, was efficiently synthesised from allylsilane (Z)-6 and aldehyde 7 via an intramolecular Sakurai cyclisation.

Stereoselective synthesis of (E)-1-iodo-1-selenoalkenes via hydroalumination-iodination of 1-alkynyl selenides

syn-Hydroalumination of 2,4,6-triisopropylphenylselanyl-1-alkynes 22 with DIBAL-H, followed by Al/I exchange with I2, afforded selectively the corresponding (E)-1-iodo-1-selenoalkenes in good yields. The sterically hindered 2,4,6-triisopropylphenyl group proved to be mandatory and prevented the formation of undesired by-products.