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    Methods in organosilane assembly

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    Genre
    Thesis/Dissertation
    Date
    2012
    Author
    Bo, Yingjian
    Advisor
    Sieburth, Scott McNeill
    Committee member
    Andrade, Rodrigo B.
    Davis, Franklin A.
    Cannon, Kevin C.
    Department
    Chemistry
    Subject
    Chemistry
    Chemistry, Organic
    Chymase Inhibitor
    Lithiation of Alkoxysilanes and Hydridosilanes
    Nk3201
    Organosilane
    Silanediol
    Sulfinimine
    Permanent link to this record
    http://hdl.handle.net/20.500.12613/821
    
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    DOI
    http://dx.doi.org/10.34944/dspace/803
    Abstract
    Dialkylsilanediols are a novel class of non-hydrolyzable analogues of the tetrahedral intermediate of amide hydrolysis, shown to be good inhibitors of HIV-1 protease, angiotensin converting enzyme (ACE), and thermolysin. An impediment to utilization of these silanediol structures, however, has been the methods for their assembly. This research describes the reductive lithiation of hydridosilanes and alkoxysilanes, and the use of the resulting silyl anions to develop efficient methods to synthesize silanediol precursors. In the first part of research, lithiation of hydridosilanes was studied. As part of this study, a simple 1H NMR method was developed for monitoring and analyzing the progress of lithiation. In addition, this method was converted to a titration for silyllithium reagents using BHT as an internal standard. Silanediols 107 and 177 are analogues of a potent chymase inhibitor, NK-3201 (82). In the second part, diphenylsilanes 108 and 170, precursors to silanediols 107 and 177, were synthesized using addition of silyllithium to sulfinimine 113 as a key step. In the third part, lithiation of alkoxysilanes was studied. (Si,O)-Dianions, generated from lithiation of silane alcohol 175 or 2,2-diphenyl-1-oxa-2-silacyclopentane (225), were reacted with a wide variety of electrophiles to give potentially useful silicon-containing building blocks. Addition of the (Si,O)-dianion 284 to sulfinimines gave silanediol inhibitor precursors with full control of stereochemistry. In the last part, a new method featuring 1,1-diphenyl-2-azaallyllithium chemistry were utilized to synthesize a series of protected α-amino silanes 323, 329 - 331.
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