Studies toward the carbanion-accelerated 6[Pi] electrocyclization : polyfunctional boronates
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[ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI AT AUTHOR'S REQUEST.] The 6π electrocyclization remains an important class of pericyclic reactions which provides access to substituted six-membered rings from uncyclized triene substrates. It was conceived that a rate acceleration of this ring closure could be accomplished via anion generation adjacent to the 6[Pi] system. In efforts to study the carbanion-accelerated 6[Pi] electrocyclization, triene substrates were prepared from cross-coupling reactions between a 2-boryl allylic sulfone and dienyl electrophiles. In addition to its application towards triene synthesis, the alkylation chemistry of the 2-boryl allylic sulfone was explored. The deprotonation of sulfones and subsequent alkylation is trivial, however, it was unclear how the reactivity of a sulfone would change as a function of a Lewis-acidic boronic ester. The development of an alkylation procedure would allow for alkylated products to undergo ring-closing metathesis, generating value added organoboron compounds that would ultimately be used to demonstrate the effectiveness polyfunctional boronates toward the synthesis of polycyclic systems.
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