Titanium-mediated [2 + 2 + 2] coupling of diynes with homoallylic alcohols |
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Authors: | Sung Moo Je Pang Jin-Hyun Park Soon-Bong Cha Jin Kun |
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Institution: | Department of Chemistry, University of Alabama, Tuscaloosa, Alabama 35487, USA. |
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Abstract: | reaction: see text] In connection with the known diyne-ene 2 + 2 + 2] cycloaddition reactions mediated by titanium aryloxides, the ability of titanium alkoxides to promote coupling of a titanacyclopentadiene with an alkene has been assessed for the isomerization-free preparation of 1,3-cyclohexadienes. The successful cycloaddition by titanium alkoxides is predicated on the use of homoallylic alcohols as the olefin component. With secondary homoallylic alcohols, high 1,3-diastereoselectivity is observed, which lends itself to enantioselective preparation of functionalized 1,3-cyclohexadienes. |
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