862133-59-3Relevant 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
Pérez-Balado, Carlos,Markó, István E.
, p. 2331 - 2349 (2007/10/03)
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
Pérez-Balado, Carlos,Lucaccioni, Fabio,Markó, István E.
, p. 4883 - 4886 (2007/10/03)
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.
A connective approach to the tetrahydropyran subunit of polycavernoside a via a novel 1,1-dianion equivalent
Pérez-Balado, Carlos,Markó, István E.
, p. 4887 - 4890 (2007/10/03)
Racemic tetrahydropyran 3 was efficiently synthesised from allylsilane 6 and aldehyde 7 via an intramolecular Sakurai cyclisation. In a single step, the relative configuration of three chiral centres was established. Allylsilane 6 was readily assembled fr
